Expeditious preparation of β- sec -alkyl vicinal amino alcohols used for chiral ligand synthesis
An economical route providing quick access to chiral β-amino alcohols bearing one β- sec -alkyl group was developed. This protocol starts with commercially available and cheap chiral sources such as derivatives of l -serine and l -threonine. A series of vicinal amino alcohols with high optical purit...
Saved in:
| Published in | Organic & biomolecular chemistry Vol. 21; no. 30; pp. 6111 - 6114 |
|---|---|
| Main Authors | , , , |
| Format | Journal Article |
| Language | English |
| Published |
CAMBRIDGE
Royal Soc Chemistry
02.08.2023
Royal Society of Chemistry |
| Subjects | |
| Online Access | Get full text |
Cover
Loading…
| Abstract | An economical route providing quick access to chiral β-amino alcohols bearing one β-
sec
-alkyl group was developed. This protocol starts with commercially available and cheap chiral sources such as derivatives of
l
-serine and
l
-threonine. A series of vicinal amino alcohols with high optical purity were prepared in good yields through 4 or 6 operationally simple steps. Two different strategies (three routes) were designed for the synthesis of amino alcohols bearing β-
sec
-alkyl groups with various steric hindrance. |
|---|---|
| AbstractList | An economical route providing quick access to chiral β-amino alcohols bearing one β-sec-alkyl group was developed. This protocol starts with commercially available and cheap chiral sources such as derivatives of l-serine and l-threonine. A series of vicinal amino alcohols with high optical purity were prepared in good yields through 4 or 6 operationally simple steps. Two different strategies (three routes) were designed for the synthesis of amino alcohols bearing β-sec-alkyl groups with various steric hindrance. An economical route providing quick access to chiral β-amino alcohols bearing one β- sec -alkyl group was developed. This protocol starts with commercially available and cheap chiral sources such as derivatives of l -serine and l -threonine. A series of vicinal amino alcohols with high optical purity were prepared in good yields through 4 or 6 operationally simple steps. Two different strategies (three routes) were designed for the synthesis of amino alcohols bearing β- sec -alkyl groups with various steric hindrance. An economical route providing quick access to chiral & beta;-amino alcohols bearing one & beta;-sec-alkyl group was developed. This protocol starts with commercially available and cheap chiral sources such as derivatives of l-serine and l-threonine. A series of vicinal amino alcohols with high optical purity were prepared in good yields through 4 or 6 operationally simple steps. Two different strategies (three routes) were designed for the synthesis of amino alcohols bearing & beta;-sec-alkyl groups with various steric hindrance. An economical route providing quick access to chiral β-amino alcohols bearing one β- -alkyl group was developed. This protocol starts with commercially available and cheap chiral sources such as derivatives of L-serine and L-threonine. A series of vicinal amino alcohols with high optical purity were prepared in good yields through 4 or 6 operationally simple steps. Two different strategies (three routes) were designed for the synthesis of amino alcohols bearing β- -alkyl groups with various steric hindrance. An economical route providing quick access to chiral β-amino alcohols bearing one β-sec-alkyl group was developed. This protocol starts with commercially available and cheap chiral sources such as derivatives of L-serine and L-threonine. A series of vicinal amino alcohols with high optical purity were prepared in good yields through 4 or 6 operationally simple steps. Two different strategies (three routes) were designed for the synthesis of amino alcohols bearing β-sec-alkyl groups with various steric hindrance.An economical route providing quick access to chiral β-amino alcohols bearing one β-sec-alkyl group was developed. This protocol starts with commercially available and cheap chiral sources such as derivatives of L-serine and L-threonine. A series of vicinal amino alcohols with high optical purity were prepared in good yields through 4 or 6 operationally simple steps. Two different strategies (three routes) were designed for the synthesis of amino alcohols bearing β-sec-alkyl groups with various steric hindrance. |
| Author | Gong, Hegui Chen, Yunrong Wu, Yu Huang, Guoqi |
| Author_xml | – sequence: 1 givenname: Guoqi surname: Huang fullname: Huang, Guoqi organization: Center for Supramolecular Chemistry and Catalysis and Department of Chemistry, College of Sciences, Shanghai University, 99 Shangda Road, Shanghai 200444, People's Republic of China – sequence: 2 givenname: Yu surname: Wu fullname: Wu, Yu organization: Center for Supramolecular Chemistry and Catalysis and Department of Chemistry, College of Sciences, Shanghai University, 99 Shangda Road, Shanghai 200444, People's Republic of China – sequence: 3 givenname: Hegui orcidid: 0000-0001-6534-5569 surname: Gong fullname: Gong, Hegui organization: Center for Supramolecular Chemistry and Catalysis and Department of Chemistry, College of Sciences, Shanghai University, 99 Shangda Road, Shanghai 200444, People's Republic of China – sequence: 4 givenname: Yunrong orcidid: 0000-0001-6872-4943 surname: Chen fullname: Chen, Yunrong organization: Center for Supramolecular Chemistry and Catalysis and Department of Chemistry, College of Sciences, Shanghai University, 99 Shangda Road, Shanghai 200444, People's Republic of China |
| BackLink | https://www.ncbi.nlm.nih.gov/pubmed/37462436$$D View this record in MEDLINE/PubMed |
| BookMark | eNqN0k9vFCEUAHBiauwfvfgBDIkXoxllgIHhWNdamzTpRc8TCg-XysIIM9r9Wv0gfiZpd7smTQ9yAcLvveQ93iHaiykCQi9b8r4lTH34xC4-EtITdvoEHbRcyoZ0TO3tzpTso8NSrghplRT8GdpnkgvKmThA-uR6BOsnn-aCxwyjzrpeIk4O_7lpcAGDGx1-rAP-5Y2POmC98jFhHUxaplDwXMBilzI2S5_rc_DfdbS4rOO0hOLLc_TU6VDgxXY_Qt8-n3xdfGnOL07PFsfnjWFtNzXWKQ2s1ZxSKqgVDIzprJJKut70gnDneiEpGEugd0pKU41tFSguO8EEO0JvNnnHnH7OUKZh5YuBEHSEWtxAe6Yo7zmTlb5-QK_SnGttt4pzIYWQXVWvtmq-XIEdxuxXOq-H--ZV8G4DfsNlcsV4iAZ2rHabUNmRTpK62qr7_9cLP919wyLNcaqhbzehJqdSMrhdWEuG2xEY_o1AxeQBNttkU9Y-PBbyF3jPr_Q |
| CitedBy_id | crossref_primary_10_1080_00304948_2024_2398466 crossref_primary_10_1002_slct_202405376 crossref_primary_10_1021_acs_orglett_3c03525 |
| Cites_doi | 10.1038/nchem.2445 10.1021/ol048386w 10.1021/jacs.1c05890 10.1039/D2CC00446A 10.1021/jacs.7b03195 10.1016/j.chempr.2018.10.006 10.1002/anie.202204907 10.3762/bjoc.16.115 10.1126/science.aaz3855 10.1038/s41467-019-11392-6 10.1021/jacs.7b03448 10.1021/jacs.0c10471 10.1021/jacs.7b01705 10.1002/anie.201610500 10.1021/ja00168a040 10.1039/C4CC02399D 10.1021/acscentsci.8b00005 10.1021/om4001549 10.1021/acs.accounts.2c00557 10.1002/ijch.201900072 10.1021/ja402922w 10.1002/anie.201512020 10.1021/ja076542z 10.1002/anie.201809310 10.1002/chem.201500094 10.1002/chem.200701636 10.1002/(SICI)1521-3773(19981116)37:21<2922::AID-ANIE2922>3.0.CO;2-1 10.1038/s41467-021-23887-2 10.1021/jm030272n 10.1038/s41467-021-21600-x 10.1021/cr9500038 10.1016/j.cclet.2015.12.021 10.1021/jacs.0c03708 10.1021/ja00141a039 10.1038/s41467-018-03535-y 10.1126/science.1249198 10.1021/ja00330a029 10.1002/anie.201704786 10.1002/1615-4169(200201)344:1<40::AID-ADSC40>3.0.CO;2-7 10.1021/acscatal.0c01842 10.1021/acscatal.1c02851 10.1039/D1SC00658D 10.1021/jm0110486 10.1016/S0957-4166(97)00375-3 10.1002/anie.200705241 10.1002/anie.202010386 10.1126/science.aaf7783 10.1039/d2cc00446a 10.1039/c4cc02399d 10.1039/d1sc00658d 10.1038/NCHEM.2445 |
| ContentType | Journal Article |
| Copyright | Copyright Royal Society of Chemistry 2023 |
| Copyright_xml | – notice: Copyright Royal Society of Chemistry 2023 |
| DBID | AAYXX CITATION 17B 1KM 1KN BLEPL BNZSX DTL EGQ NPM 7QO 7T7 7TM 8FD C1K FR3 P64 7X8 |
| DOI | 10.1039/D3OB00803G |
| DatabaseName | CrossRef Web of Knowledge Index Chemicus Current Chemical Reactions Web of Science Core Collection Web of Science - Science Citation Index Expanded - 2023 Science Citation Index Expanded Web of Science Primary (SCIE, SSCI & AHCI) PubMed Biotechnology Research Abstracts Industrial and Applied Microbiology Abstracts (Microbiology A) Nucleic Acids Abstracts Technology Research Database Environmental Sciences and Pollution Management Engineering Research Database Biotechnology and BioEngineering Abstracts MEDLINE - Academic |
| DatabaseTitle | CrossRef Web of Science PubMed Biotechnology Research Abstracts Technology Research Database Nucleic Acids Abstracts Engineering Research Database Industrial and Applied Microbiology Abstracts (Microbiology A) Biotechnology and BioEngineering Abstracts Environmental Sciences and Pollution Management MEDLINE - Academic |
| DatabaseTitleList | Biotechnology Research Abstracts CrossRef Web of Science PubMed MEDLINE - Academic |
| Database_xml | – sequence: 1 dbid: NPM name: PubMed url: https://proxy.k.utb.cz/login?url=http://www.ncbi.nlm.nih.gov/entrez/query.fcgi?db=PubMed sourceTypes: Index Database – sequence: 2 dbid: 1KN name: Current Chemical Reactions url: https://proxy.k.utb.cz/login?url=https://www.webofscience.com/wos/woscc/search-with-editions?editions=WOS.CCR sourceTypes: Enrichment Source Index Database |
| DeliveryMethod | fulltext_linktorsrc |
| Discipline | Chemistry |
| EISSN | 1477-0539 |
| EndPage | 6114 |
| ExternalDocumentID | 37462436 001027505700001 10_1039_D3OB00803G |
| Genre | Journal Article |
| GrantInformation_xml | – fundername: National Natural Science Foundation of China; National Natural Science Foundation of China (NSFC) grantid: 21871173; 21901162 |
| GroupedDBID | --- -DZ -~X 0-7 0R~ 123 29N 4.4 705 70~ 7~J AAEMU AAIWI AAJAE AAMEH AANOJ AAWGC AAXHV AAXPP AAYXX ABASK ABDVN ABEMK ABJNI ABPDG ABRYZ ABXOH ACGFS ACIWK ACLDK ACNCT ACPRK ADMRA ADSRN AEFDR AENEX AENGV AESAV AETIL AFLYV AFOGI AFRAH AFRDS AFRZK AFVBQ AGEGJ AGKEF AGRSR AHGCF AKMSF ALMA_UNASSIGNED_HOLDINGS ALUYA ANUXI APEMP ASKNT AUDPV BLAPV BSQNT C6K CITATION CS3 D0L DU5 EBS ECGLT EE0 EF- F5P GGIMP GNO H13 HZ~ H~N IDZ J3I M4U N9A O9- P2P R56 R7B R7C RAOCF RCNCU RNS RPMJG RRA RRC RSCEA SKA SKF SLH TN5 TWZ VH6 WH7 XSW YNT YZZ 17B 1KM 1KN BLEPL DTL GROUPED_WOS_SCIENCE_CITATION_INDEX_EXPANDED GROUPED_WOS_WEB_OF_SCIENCE NPM 7QO 7T7 7TM 8FD C1K FR3 P64 7X8 |
| ID | FETCH-LOGICAL-c315t-df9ae31a422262d63ecc5d9797f8c8604ff8672ecd0e8f977cd63d19e94756363 |
| ISICitedReferencesCount | 3 |
| ISICitedReferencesURI | https://gateway.webofknowledge.com/gateway/Gateway.cgi?GWVersion=2&SrcApp=Summon&SrcAuth=ProQuest&DestApp=WOS&DestLinkType=CitingArticles&UT=001027505700001 |
| ISSN | 1477-0520 1477-0539 |
| IngestDate | Fri Jul 11 01:53:08 EDT 2025 Mon Jun 30 12:01:24 EDT 2025 Thu Apr 03 07:25:22 EDT 2025 Fri May 30 08:11:17 EDT 2025 Fri Aug 29 16:13:38 EDT 2025 Tue Jul 01 01:52:29 EDT 2025 Thu Apr 24 22:57:07 EDT 2025 |
| IsPeerReviewed | true |
| IsScholarly | true |
| Issue | 30 |
| Keywords | CATALYSIS POTENT NICKEL PHOTOREDOX ACIDS ARYLATION ISOMERIZATION ASYMMETRIC HYDROGENATION DERIVATIVES ALLYLAMINES |
| Language | English |
| LinkModel | OpenURL |
| LogoURL | https://exlibris-pub.s3.amazonaws.com/fromwos-v2.jpg |
| MergedId | FETCHMERGED-LOGICAL-c315t-df9ae31a422262d63ecc5d9797f8c8604ff8672ecd0e8f977cd63d19e94756363 |
| Notes | ObjectType-Article-1 SourceType-Scholarly Journals-1 ObjectType-Feature-2 content type line 14 content type line 23 |
| ORCID | 0000-0001-6534-5569 0000-0001-6872-4943 |
| PMID | 37462436 |
| PQID | 2844676675 |
| PQPubID | 2047497 |
| PageCount | 4 |
| ParticipantIDs | crossref_citationtrail_10_1039_D3OB00803G proquest_miscellaneous_2839248437 webofscience_primary_001027505700001CitationCount pubmed_primary_37462436 webofscience_primary_001027505700001 crossref_primary_10_1039_D3OB00803G proquest_journals_2844676675 |
| ProviderPackageCode | CITATION AAYXX |
| PublicationCentury | 2000 |
| PublicationDate | 2023-08-02 |
| PublicationDateYYYYMMDD | 2023-08-02 |
| PublicationDate_xml | – month: 08 year: 2023 text: 2023-08-02 day: 02 |
| PublicationDecade | 2020 |
| PublicationPlace | CAMBRIDGE |
| PublicationPlace_xml | – name: CAMBRIDGE – name: England – name: Cambridge |
| PublicationTitle | Organic & biomolecular chemistry |
| PublicationTitleAbbrev | ORG BIOMOL CHEM |
| PublicationTitleAlternate | Org Biomol Chem |
| PublicationYear | 2023 |
| Publisher | Royal Soc Chemistry Royal Society of Chemistry |
| Publisher_xml | – name: Royal Soc Chemistry – name: Royal Society of Chemistry |
| References | He (D3OB00803G/cit12a/1) 2020; 59 Menges (D3OB00803G/cit22/1) 2002; 344 Huo (D3OB00803G/cit2/1) 2020; 367 Poremba (D3OB00803G/cit3a/1) 2020; 10 Qi (D3OB00803G/cit10/1) 2021; 143 Li (D3OB00803G/cit4b/1) 2019; 5 Sahari (D3OB00803G/cit17/1) 2022; 58 Vasseur (D3OB00803G/cit5c/1) 2016; 8 Gridnev (D3OB00803G/cit8a/1) 2008; 130 Ager (D3OB00803G/cit1a/1) 1996; 96 Berton (D3OB00803G/cit18/1) 2020; 16 Cheng (D3OB00803G/cit6d/1) 2019; 10 Ju (D3OB00803G/cit16/1) 2017; 56 Collado (D3OB00803G/cit19/1) 2002; 45 Sommer (D3OB00803G/cit5b/1) 2018; 4 Wu (D3OB00803G/cit8b/1) 2004; 6 Burk (D3OB00803G/cit8c/1) 1995; 117 Lu (D3OB00803G/cit11c/1) 2016; 27 Girard (D3OB00803G/cit24c/1) 1998; 37 Beemelmanns (D3OB00803G/cit15/1) 2015; 21 Satyanarayana (D3OB00803G/cit24b/1) 2009; 48 Wang (D3OB00803G/cit7/1) 2021; 12 Mayer (D3OB00803G/cit24a/1) 2022; 55 Poremba (D3OB00803G/cit12c/1) 2017; 139 Zhang (D3OB00803G/cit1b/1) 2016; 353 Diéguez (D3OB00803G/cit21/1) 2008; 14 Inoue (D3OB00803G/cit20c/1) 1990; 112 Cherney (D3OB00803G/cit3b/1) 2013; 135 Li (D3OB00803G/cit11b/1) 2016; 55 Tani (D3OB00803G/cit20d/1) 1984; 106 Avalos (D3OB00803G/cit24d/1) 1997; 8 Huan (D3OB00803G/cit6a/1) 2021; 12 Shatskiy (D3OB00803G/cit9a/1) 2021; 12 Huang (D3OB00803G/cit13/1) 2022; 61 García-Domínguez (D3OB00803G/cit4c/1) 2017; 139 Shu (D3OB00803G/cit6c/1) 2020; 142 Hu (D3OB00803G/cit14/1) 2003; 46 Wu (D3OB00803G/cit20b/1) 2017; 56 Woods (D3OB00803G/cit12b/1) 2017; 139 Larionov (D3OB00803G/cit5d/1) 2014; 50 He (D3OB00803G/cit11a/1) 2014; 343 Wu (D3OB00803G/cit20a/1) 2018; 9 De Crisci (D3OB00803G/cit23/1) 2013; 32 Cheng (D3OB00803G/cit6b/1) 2021; 11 Tu (D3OB00803G/cit4a/1) 2020; 142 Janssen-Müller (D3OB00803G/cit5a/1) 2020; 60 Ni (D3OB00803G/cit9b/1) 2018; 57 García-Domínguez, A (WOS:000402498500014) 2017; 139 Wu, Z (WOS:000394997700035) 2017; 56 He, YL (WOS:000572782100001) 2020; 59 Beemelmanns, C (WOS:000355260000018) 2015; 21 Shu, XM (WOS:000588273900011) 2020; 142 Huan, LT (WOS:000663747800026) 2021; 12 Sommer, H (WOS:000426613700007) 2018; 4 Lu, X (WOS:000374799400001) 2016; 27 Menges, F (WOS:000174488300006) 2002; 344 Sahari, A (WOS:000754652400001) 2022; 58 Mayer, LC (WOS:000884814800001) 2022; 55 Vasseur, A (WOS:000370824300007) 2016; 8 Ager, DJ (WOS:A1996UC45100008) 1996; 96 He, J (WOS:000332728500029) 2014; 343 Wang, JW (WOS:000624978300024) 2021; 12 Cheng, XK (WOS:000693621800037) 2021; 11 Li, SH (WOS:000373006100030) 2016; 55 Avalos, M (WOS:A1997XZ44200001) 1997; 8 Poremba, KE (WOS:000400321500013) 2017; 139 Cheng, XK (WOS:000479030800007) 2019; 10 Woods, BP (WOS:000400321500014) 2017; 139 Zhang, W (WOS:000382558900035) 2016; 353 TANI, K (WOS:A1984TH18100029) 1984; 106 Huang, WJ (WOS:000813608600001) 2022; 61 Qi, RP (WOS:000686555000043) 2021; 143 Wu, HP (WOS:000224112000055) 2004; 6 Ju, M (WOS:000406798700056) 2017; 56 Girard, C (WOS:000077114900001) 1998; 37 De Crisci, AG (WOS:000317370000028) 2013; 32 Hu, XE (WOS:000184719100012) 2003; 46 Poremba, KE (WOS:000562075000021) 2020; 10 Janssen-Müller, D (WOS:000482440200001) 2020; 60 Berton, M (WOS:000541443800001) 2020; 16 Wu, Z (WOS:000428039500003) 2018; 9 Cherney, AH (WOS:000319551000014) 2013; 135 Ni, SY (WOS:000448049800026) 2018; 57 Dieguez, M (WOS:000255702800020) 2008; 14 INOUE, S (WOS:A1990DH27700040) 1990; 112 Li, JS (WOS:000455452800016) 2019; 5 Collado, I (WOS:000177346400009) 2002; 45 BURK, MJ (WOS:A1995RU81800039) 1995; 117 Gridnev, ID (WOS:000253400900056) 2008; 130 Tu, HY (WOS:000537734000006) 2020; 142 Shatskiy, A (WOS:000631711500001) 2021; 12 Huo, HH (WOS:000512377600038) 2020; 367 Satyanarayana, T (WOS:000262539800004) 2009; 48 Larionov, E (WOS:000340513400002) 2014; 50 |
| References_xml | – volume: 8 start-page: 209 year: 2016 ident: D3OB00803G/cit5c/1 publication-title: Nat. Chem. doi: 10.1038/nchem.2445 – volume: 6 start-page: 3645 year: 2004 ident: D3OB00803G/cit8b/1 publication-title: Org. Lett. doi: 10.1021/ol048386w – volume: 143 start-page: 12777 year: 2021 ident: D3OB00803G/cit10/1 publication-title: J. Am. Chem. Soc. doi: 10.1021/jacs.1c05890 – volume: 58 start-page: 3027 year: 2022 ident: D3OB00803G/cit17/1 publication-title: Chem. Commun. doi: 10.1039/D2CC00446A – volume: 139 start-page: 6835 year: 2017 ident: D3OB00803G/cit4c/1 publication-title: J. Am. Chem. Soc. doi: 10.1021/jacs.7b03195 – volume: 5 start-page: 192 year: 2019 ident: D3OB00803G/cit4b/1 publication-title: Chem doi: 10.1016/j.chempr.2018.10.006 – volume: 61 start-page: e202204907 year: 2022 ident: D3OB00803G/cit13/1 publication-title: Angew. Chem., Int. Ed. doi: 10.1002/anie.202204907 – volume: 16 start-page: 1343 year: 2020 ident: D3OB00803G/cit18/1 publication-title: Beilstein J. Org. Chem. doi: 10.3762/bjoc.16.115 – volume: 367 start-page: 559 year: 2020 ident: D3OB00803G/cit2/1 publication-title: Science doi: 10.1126/science.aaz3855 – volume: 10 start-page: 3549 year: 2019 ident: D3OB00803G/cit6d/1 publication-title: Nat. Commun. doi: 10.1038/s41467-019-11392-6 – volume: 139 start-page: 5688 year: 2017 ident: D3OB00803G/cit12b/1 publication-title: J. Am. Chem. Soc. doi: 10.1021/jacs.7b03448 – volume: 142 start-page: 19058 year: 2020 ident: D3OB00803G/cit6c/1 publication-title: J. Am. Chem. Soc. doi: 10.1021/jacs.0c10471 – volume: 139 start-page: 5684 year: 2017 ident: D3OB00803G/cit12c/1 publication-title: J. Am. Chem. Soc. doi: 10.1021/jacs.7b01705 – volume: 56 start-page: 1371 year: 2017 ident: D3OB00803G/cit20b/1 publication-title: Angew. Chem., Int. Ed. doi: 10.1002/anie.201610500 – volume: 112 start-page: 4897 year: 1990 ident: D3OB00803G/cit20c/1 publication-title: J. Am. Chem. Soc. doi: 10.1021/ja00168a040 – volume: 50 start-page: 9816 year: 2014 ident: D3OB00803G/cit5d/1 publication-title: Chem. Commun. doi: 10.1039/C4CC02399D – volume: 4 start-page: 153 year: 2018 ident: D3OB00803G/cit5b/1 publication-title: ACS Cent. Sci. doi: 10.1021/acscentsci.8b00005 – volume: 32 start-page: 2257 year: 2013 ident: D3OB00803G/cit23/1 publication-title: Organometallics doi: 10.1021/om4001549 – volume: 55 start-page: 3345 year: 2022 ident: D3OB00803G/cit24a/1 publication-title: Acc. Chem. Res. doi: 10.1021/acs.accounts.2c00557 – volume: 60 start-page: 195 year: 2020 ident: D3OB00803G/cit5a/1 publication-title: Isr. J. Chem. doi: 10.1002/ijch.201900072 – volume: 135 start-page: 7442 year: 2013 ident: D3OB00803G/cit3b/1 publication-title: J. Am. Chem. Soc. doi: 10.1021/ja402922w – volume: 55 start-page: 4317 year: 2016 ident: D3OB00803G/cit11b/1 publication-title: Angew. Chem., Int. Ed. doi: 10.1002/anie.201512020 – volume: 130 start-page: 2560 year: 2008 ident: D3OB00803G/cit8a/1 publication-title: J. Am. Chem. Soc. doi: 10.1021/ja076542z – volume: 57 start-page: 14560 year: 2018 ident: D3OB00803G/cit9b/1 publication-title: Angew. Chem., Int. Ed. doi: 10.1002/anie.201809310 – volume: 21 start-page: 8416 year: 2015 ident: D3OB00803G/cit15/1 publication-title: Chem. – Eur. J. doi: 10.1002/chem.201500094 – volume: 14 start-page: 3653 year: 2008 ident: D3OB00803G/cit21/1 publication-title: Chem. – Eur. J. doi: 10.1002/chem.200701636 – volume: 37 start-page: 2922 year: 1998 ident: D3OB00803G/cit24c/1 publication-title: Angew. Chem., Int. Ed. doi: 10.1002/(SICI)1521-3773(19981116)37:21<2922::AID-ANIE2922>3.0.CO;2-1 – volume: 12 start-page: 3536 year: 2021 ident: D3OB00803G/cit6a/1 publication-title: Nat. Commun. doi: 10.1038/s41467-021-23887-2 – volume: 46 start-page: 3655 year: 2003 ident: D3OB00803G/cit14/1 publication-title: J. Med. Chem. doi: 10.1021/jm030272n – volume: 12 start-page: 1313 year: 2021 ident: D3OB00803G/cit7/1 publication-title: Nat. Commun. doi: 10.1038/s41467-021-21600-x – volume: 96 start-page: 835 year: 1996 ident: D3OB00803G/cit1a/1 publication-title: Chem. Rev. doi: 10.1021/cr9500038 – volume: 27 start-page: 305 year: 2016 ident: D3OB00803G/cit11c/1 publication-title: Chin. Chem. Lett. doi: 10.1016/j.cclet.2015.12.021 – volume: 142 start-page: 9604 year: 2020 ident: D3OB00803G/cit4a/1 publication-title: J. Am. Chem. Soc. doi: 10.1021/jacs.0c03708 – volume: 117 start-page: 9375 year: 1995 ident: D3OB00803G/cit8c/1 publication-title: J. Am. Chem. Soc. doi: 10.1021/ja00141a039 – volume: 9 start-page: 1185 year: 2018 ident: D3OB00803G/cit20a/1 publication-title: Nat. Commun. doi: 10.1038/s41467-018-03535-y – volume: 343 start-page: 1216 year: 2014 ident: D3OB00803G/cit11a/1 publication-title: Science doi: 10.1126/science.1249198 – volume: 106 start-page: 5208 year: 1984 ident: D3OB00803G/cit20d/1 publication-title: J. Am. Chem. Soc. doi: 10.1021/ja00330a029 – volume: 56 start-page: 9944 year: 2017 ident: D3OB00803G/cit16/1 publication-title: Angew. Chem., Int. Ed. doi: 10.1002/anie.201704786 – volume: 344 start-page: 40 year: 2002 ident: D3OB00803G/cit22/1 publication-title: Adv. Synth. Catal. doi: 10.1002/1615-4169(200201)344:1<40::AID-ADSC40>3.0.CO;2-7 – volume: 10 start-page: 8237 year: 2020 ident: D3OB00803G/cit3a/1 publication-title: ACS Catal. doi: 10.1021/acscatal.0c01842 – volume: 11 start-page: 11059 year: 2021 ident: D3OB00803G/cit6b/1 publication-title: ACS Catal. doi: 10.1021/acscatal.1c02851 – volume: 12 start-page: 5430 year: 2021 ident: D3OB00803G/cit9a/1 publication-title: Chem. Sci. doi: 10.1039/D1SC00658D – volume: 45 start-page: 3619 year: 2002 ident: D3OB00803G/cit19/1 publication-title: J. Med. Chem. doi: 10.1021/jm0110486 – volume: 8 start-page: 2997 year: 1997 ident: D3OB00803G/cit24d/1 publication-title: Tetrahedron: Asymmetry doi: 10.1016/S0957-4166(97)00375-3 – volume: 48 start-page: 456 year: 2009 ident: D3OB00803G/cit24b/1 publication-title: Angew. Chem., Int. Ed. doi: 10.1002/anie.200705241 – volume: 59 start-page: 21530 year: 2020 ident: D3OB00803G/cit12a/1 publication-title: Angew. Chem., Int. Ed. doi: 10.1002/anie.202010386 – volume: 353 start-page: 1014 year: 2016 ident: D3OB00803G/cit1b/1 publication-title: Science doi: 10.1126/science.aaf7783 – volume: 142 start-page: 9604 year: 2020 ident: WOS:000537734000006 article-title: Enantioselective Three-Component Fluoroalkylarylation of Unactivated Olefins through Nickel-Catalyzed Cross-Electrophile Coupling publication-title: JOURNAL OF THE AMERICAN CHEMICAL SOCIETY doi: 10.1021/jacs.0c03708 – volume: 56 start-page: 9944 year: 2017 ident: WOS:000406798700056 article-title: Chemo- and Enantioselective Intramolecular Silver-Catalyzed Aziridinations publication-title: ANGEWANDTE CHEMIE-INTERNATIONAL EDITION doi: 10.1002/anie.201704786 – volume: 48 start-page: 456 year: 2009 ident: WOS:000262539800004 article-title: Nonlinear Effects In Asymmetric Catalysis publication-title: ANGEWANDTE CHEMIE-INTERNATIONAL EDITION doi: 10.1002/anie.200705241 – volume: 5 start-page: 192 year: 2019 ident: WOS:000455452800016 article-title: Photoredox-Catalysis-Modulated, Nickel-Catalyzed Divergent Difunctionalization of Ethylene publication-title: CHEM doi: 10.1016/j.chempr.2018.10.006 – volume: 61 start-page: ARTN e202204907 year: 2022 ident: WOS:000813608600001 article-title: Total Synthesis of Complex Peptidyl Nucleoside Antibiotics: Asymmetric De Novo Syntheses of Miharamycin B and Its Biosynthetic Precursor publication-title: ANGEWANDTE CHEMIE-INTERNATIONAL EDITION doi: 10.1002/anie.202204907 – volume: 46 start-page: 3655 year: 2003 ident: WOS:000184719100012 article-title: Discovery of (3S)-amino-(4R)-ethylpiperidinyl quinolones as potent antibacterial agents with a broad spectrum of activity and activity against resistant pathogens publication-title: JOURNAL OF MEDICINAL CHEMISTRY doi: 10.1021/jm030272n – volume: 130 start-page: 2560 year: 2008 ident: WOS:000253400900056 article-title: Asymmetric hydrogenation catalyzed by a rhodium complex of (R)-(tert-butylmethylphosphino)(di-tert-butylphosphino)methane:: Scope of enantioselectivity and mechanistic study publication-title: JOURNAL OF THE AMERICAN CHEMICAL SOCIETY doi: 10.1021/ja076542z – volume: 55 start-page: 3345 year: 2022 ident: WOS:000884814800001 article-title: Nonlinear Effects in Asymmetric Catalysis by Design: Concept, Synthesis, and Applications publication-title: ACCOUNTS OF CHEMICAL RESEARCH doi: 10.1021/acs.accounts.2c00557 – volume: 12 start-page: ARTN 3536 year: 2021 ident: WOS:000663747800026 article-title: Asymmetric benzylic C(sp3)-H acylation via dual nickel and photoredox catalysis publication-title: NATURE COMMUNICATIONS doi: 10.1038/s41467-021-23887-2 – volume: 27 start-page: 305 year: 2016 ident: WOS:000374799400001 article-title: Synthesis of unnatural amino acids through palladium-catalyzed C(sp3)-H functionalization publication-title: CHINESE CHEMICAL LETTERS doi: 10.1016/j.cclet.2015.12.021 – volume: 58 start-page: 3027 year: 2022 ident: WOS:000754652400001 article-title: Titanium isopropoxide-mediated cis-selective synthesis of 3,4-substituted butyrolactones from CO2 publication-title: CHEMICAL COMMUNICATIONS doi: 10.1039/d2cc00446a – volume: 135 start-page: 7442 year: 2013 ident: WOS:000319551000014 article-title: Catalytic Asymmetric Reductive Acyl Cross-Coupling: Synthesis of Enantioenriched Acyclic α,α-Disubstituted Ketones publication-title: JOURNAL OF THE AMERICAN CHEMICAL SOCIETY doi: 10.1021/ja402922w – volume: 32 start-page: 2257 year: 2013 ident: WOS:000317370000028 article-title: Chemoselective Oxidation of Polyols with Chiral Palladium Catalysts publication-title: ORGANOMETALLICS doi: 10.1021/om4001549 – volume: 10 start-page: ARTN 3549 year: 2019 ident: WOS:000479030800007 article-title: Enantioselective benzylic C-H arylation via photoredox and nickel dual catalysis publication-title: NATURE COMMUNICATIONS doi: 10.1038/s41467-019-11392-6 – volume: 142 start-page: 19058 year: 2020 ident: WOS:000588273900011 article-title: Direct Enantioselective C(sp3)-H Acylation for the Synthesis of α-Amino Ketones publication-title: JOURNAL OF THE AMERICAN CHEMICAL SOCIETY doi: 10.1021/jacs.0c10471 – volume: 45 start-page: 3619 year: 2002 ident: WOS:000177346400009 article-title: (2S,1′S,2′S,3′R)-2-(2′-carboxy-3′-methylcyclopropyl) glycine is a potent and selective metabotropic group 2 receptor agonist with anxiolytic properties publication-title: JOURNAL OF MEDICINAL CHEMISTRY doi: 10.1021/jm0110486 – volume: 50 start-page: 9816 year: 2014 ident: WOS:000340513400002 article-title: Well-defined transition metal hydrides in catalytic isomerizations publication-title: CHEMICAL COMMUNICATIONS doi: 10.1039/c4cc02399d – volume: 56 start-page: 1371 year: 2017 ident: WOS:000394997700035 article-title: Rhodium-Catalyzed Asymmetric Synthesis of β-Branched Amides publication-title: ANGEWANDTE CHEMIE-INTERNATIONAL EDITION doi: 10.1002/anie.201610500 – volume: 143 start-page: 12777 year: 2021 ident: WOS:000686555000043 article-title: Visible Light Induced Cu-Catalyzed Asymmetric C(sp3)-H Alkylation publication-title: JOURNAL OF THE AMERICAN CHEMICAL SOCIETY doi: 10.1021/jacs.1c05890 – volume: 21 start-page: 8416 year: 2015 ident: WOS:000355260000018 article-title: Evolution of a Short Route to Strychnine by Using the Samarium-Diiodide-Induced Cascade Cyclization as a Key Step publication-title: CHEMISTRY-A EUROPEAN JOURNAL doi: 10.1002/chem.201500094 – volume: 353 start-page: 1014 year: 2016 ident: WOS:000382558900035 article-title: Enantioselective cyanation of benzylic C-H bonds via copper-catalyzed radical relay publication-title: SCIENCE – volume: 139 start-page: 6835 year: 2017 ident: WOS:000402498500014 article-title: Nickel-Catalyzed Reductive Dicarbofunctionalization of Alkenes publication-title: JOURNAL OF THE AMERICAN CHEMICAL SOCIETY doi: 10.1021/jacs.7b03195 – volume: 367 start-page: 559 year: 2020 ident: WOS:000512377600038 article-title: Catalyst-controlled doubly enantioconvergent coupling of racemic alkyl nucleophiles and electrophiles publication-title: SCIENCE doi: 10.1126/science.aaz3855 – volume: 117 start-page: 9375 year: 1995 ident: WOS:A1995RU81800039 article-title: ASYMMETRIC CATALYTIC SYNTHESIS OF BETA-BRANCHED AMINO-ACIDS VIA HIGHLY ENANTIOSELECTIVE HYDROGENATION REACTIONS publication-title: JOURNAL OF THE AMERICAN CHEMICAL SOCIETY – volume: 59 start-page: 21530 year: 2020 ident: WOS:000572782100001 article-title: Enantio- and Regioselective NiH-Catalyzed Reductive Hydroarylation of Vinylarenes with Aryl Iodides publication-title: ANGEWANDTE CHEMIE-INTERNATIONAL EDITION doi: 10.1002/anie.202010386 – volume: 343 start-page: 1216 year: 2014 ident: WOS:000332728500029 article-title: Ligand-Controlled C(sp3)-H Arylation and Olefination in Synthesis of Unnatural Chiral α-Amino Acids publication-title: SCIENCE doi: 10.1126/science.1249198 – volume: 57 start-page: 14560 year: 2018 ident: WOS:000448049800026 article-title: A General Amino Acid Synthesis Enabled by Innate Radical Cross-Coupling publication-title: ANGEWANDTE CHEMIE-INTERNATIONAL EDITION doi: 10.1002/anie.201809310 – volume: 4 start-page: 153 year: 2018 ident: WOS:000426613700007 article-title: Walking Metals for Remote Functionalization publication-title: ACS CENTRAL SCIENCE doi: 10.1021/acscentsci.8b00005 – volume: 12 start-page: 5430 year: 2021 ident: WOS:000631711500001 article-title: Stereoselective synthesis of unnatural α-amino acid derivatives through photoredox catalysis publication-title: CHEMICAL SCIENCE doi: 10.1039/d1sc00658d – volume: 9 start-page: ARTN 1185 year: 2018 ident: WOS:000428039500003 article-title: Asymmetric synthesis of γ-branched amines via rhodium-catalyzed reductive amination publication-title: NATURE COMMUNICATIONS doi: 10.1038/s41467-018-03535-y – volume: 11 start-page: 11059 year: 2021 ident: WOS:000693621800037 article-title: Stereo- and Enantioselective Benzylic C-H Alkenylation via Photoredox/Nickel Dual Catalysis publication-title: ACS CATALYSIS doi: 10.1021/acscatal.1c02851 – volume: 60 start-page: 195 year: 2020 ident: WOS:000482440200001 article-title: Tackling Remote sp3 C-H Functionalization via Ni-Catalyzed "chain-walking" Reactions publication-title: ISRAEL JOURNAL OF CHEMISTRY doi: 10.1002/ijch.201900072 – volume: 37 start-page: 2923 year: 1998 ident: WOS:000077114900001 article-title: Nonlinear effects in asymmetric synthesis and stereoselective reactions: Ten years of investigation publication-title: ANGEWANDTE CHEMIE-INTERNATIONAL EDITION – volume: 12 start-page: ARTN 1313 year: 2021 ident: WOS:000624978300024 article-title: Catalytic asymmetric reductive hydroalkylation of enamides and enecarbamates to chiral aliphatic amines publication-title: NATURE COMMUNICATIONS doi: 10.1038/s41467-021-21600-x – volume: 112 start-page: 4897 year: 1990 ident: WOS:A1990DH27700040 article-title: MECHANISM OF THE ASYMMETRIC ISOMERIZATION OF ALLYLAMINES TO ENAMINES CATALYZED BY 2,2'-BIS(DIPHENYLPHOSPHINO)-1,1'-BINAPHTHYL RHODIUM COMPLEXES publication-title: JOURNAL OF THE AMERICAN CHEMICAL SOCIETY – volume: 106 start-page: 5208 year: 1984 ident: WOS:A1984TH18100029 article-title: METAL-ASSISTED TERPENOID SYNTHESIS .7. HIGHLY ENANTIOSELECTIVE ISOMERIZATION OF PROCHIRAL ALLYLAMINES CATALYZED BY CHIRAL DIPHOSPHINE RHODIUM(I) COMPLEXES - PREPARATION OF OPTICALLY-ACTIVE ENAMINES publication-title: JOURNAL OF THE AMERICAN CHEMICAL SOCIETY – volume: 139 start-page: 5688 year: 2017 ident: WOS:000400321500014 article-title: Nickel-Catalyzed Enantioselective Reductive Cross-Coupling of Styrenyl Aziridines publication-title: JOURNAL OF THE AMERICAN CHEMICAL SOCIETY doi: 10.1021/jacs.7b03448 – volume: 139 start-page: 5684 year: 2017 ident: WOS:000400321500013 article-title: Nickel-Catalyzed Asymmetric Reductive Cross-Coupling To Access 1,1-Diarylalkanes publication-title: JOURNAL OF THE AMERICAN CHEMICAL SOCIETY doi: 10.1021/jacs.7b01705 – volume: 55 start-page: 4317 year: 2016 ident: WOS:000373006100030 article-title: Ligand-Enabled Arylation of -C-H Bonds publication-title: ANGEWANDTE CHEMIE-INTERNATIONAL EDITION doi: 10.1002/anie.201512020 – volume: 14 start-page: 3653 year: 2008 ident: WOS:000255702800020 article-title: modular phosphite-oxazoline/oxazine ligand library for asymmetric Pd-catalyzed allylic substitution reactions: Scope and limitations - Origin of enantioselectivity publication-title: CHEMISTRY-A EUROPEAN JOURNAL doi: 10.1002/chem.200701636 – volume: 344 start-page: 40 year: 2002 ident: WOS:000174488300006 article-title: Threonine-derived phosphinite-oxazoline ligands for the Ir-catalyzed enantioselective hydrogenation publication-title: ADVANCED SYNTHESIS & CATALYSIS – volume: 10 start-page: 8237 year: 2020 ident: WOS:000562075000021 article-title: Nickel-Catalyzed Enantioselective Reductive Cross-Coupling Reactions publication-title: ACS CATALYSIS doi: 10.1021/acscatal.0c01842 – volume: 8 start-page: 2997 year: 1997 ident: WOS:A1997XZ44200001 article-title: Nonlinear stereochemical effects in asymmetric reactions publication-title: TETRAHEDRON-ASYMMETRY – volume: 16 start-page: 1343 year: 2020 ident: WOS:000541443800001 article-title: Disposable cartridge concept for the on-demand synthesis of turbo Grignards, Knochel-Hauser amides, and magnesium alkoxides publication-title: BEILSTEIN JOURNAL OF ORGANIC CHEMISTRY doi: 10.3762/bjoc.16.115 – volume: 6 start-page: 3645 year: 2004 ident: WOS:000224112000055 article-title: Highly enantioselective asymmetric hydrogenation of β-acetamido dehydroamino acid derivatives using a three-hindered quadrant rhodium catalyst publication-title: ORGANIC LETTERS doi: 10.1021/ol048386w – volume: 8 start-page: 209 year: 2016 ident: WOS:000370824300007 article-title: Remote functionalization through alkene isomerization publication-title: NATURE CHEMISTRY doi: 10.1038/NCHEM.2445 – volume: 96 start-page: 835 year: 1996 ident: WOS:A1996UC45100008 article-title: 1,2-amino alcohols and their heterocyclic derivatives as chiral auxiliaries in asymmetric synthesis publication-title: CHEMICAL REVIEWS |
| SSID | ssj0019764 |
| Score | 2.421362 |
| Snippet | An economical route providing quick access to chiral β-amino alcohols bearing one β-
sec
-alkyl group was developed. This protocol starts with commercially... An economical route providing quick access to chiral & beta;-amino alcohols bearing one & beta;-sec-alkyl group was developed. This protocol starts with... An economical route providing quick access to chiral β-amino alcohols bearing one β- -alkyl group was developed. This protocol starts with commercially... An economical route providing quick access to chiral β-amino alcohols bearing one β-sec-alkyl group was developed. This protocol starts with commercially... |
| Source | Web of Science |
| SourceID | proquest pubmed webofscience crossref |
| SourceType | Aggregation Database Index Database Enrichment Source |
| StartPage | 6111 |
| SubjectTerms | Alcohols Chemistry Chemistry, Organic L-Serine Physical Sciences Science & Technology Steric hindrance Synthesis Threonine |
| Title | Expeditious preparation of β- sec -alkyl vicinal amino alcohols used for chiral ligand synthesis |
| URI | http://gateway.webofknowledge.com/gateway/Gateway.cgi?GWVersion=2&SrcApp=Summon&SrcAuth=ProQuest&DestApp=WOS&DestLinkType=FullRecord&UT=001027505700001 https://www.ncbi.nlm.nih.gov/pubmed/37462436 https://www.proquest.com/docview/2844676675 https://www.proquest.com/docview/2839248437 |
| Volume | 21 |
| WOS | 001027505700001 |
| WOSCitedRecordID | wos001027505700001 |
| hasFullText | 1 |
| inHoldings | 1 |
| isFullTextHit | |
| isPrint | |
| link | http://utb.summon.serialssolutions.com/2.0.0/link/0/eLvHCXMwnV1fb9MwELegk2AviP8EBjJie0BVoI1dO3ncSllB_HnppPFUJbZTIrp0Wxqk8bH4IHwm7mwnLVCkwUtUxZdaufvZ-Z19dyZkF-uraIBK2GeZDrmK0zCLIhhXaR4rJXtK5Zgo_P6DGB_xt8eD4-ZIeJ9dssxeqG8b80r-x6pwD-yKWbL_YNn2T-EG_Ab7whUsDNdL2RjrFGuMuaorTPZ3ZbwdAdwbjvYOorBbGdUN0_mXi3n3K26iY2mAk6JcdFN3Nm7VrSvgnBhsqD4XmK0_L2Z2Mf2iBG5YFdU6fXWZm8riBRP3m7N14Vl_btwKJn4h-rBenBXt1F_bKb9uo358QPDYzOpWaOgTRj5hoKL_sPp1iYjZqDg3sRo3l3IpQxjjycaZusew0KlmiwxJK5utC4GWT0-szZjkIuLst2LZ7vPrm66SrQhchKhDtvZHkzfv2j0kIFq8KUjLkperrrbJtebhX9nIHy7GRjZimcfkJrnhXQa67-x_i1wx5W1yfdho_A5J13BA13BAFzn98T2kgAHqMEA9BqjFAG0wQBEDFDBAHQaowwBtMXCXHL0eTYbj0B-dESrWHyxDnSepYf0UF_hEpAWDkTrQiUwkDMFY9Hiex0JGRumeiXPwARTI6H5iEi4Hggl2j3TKRWkeEGqiJMtUmglpGKZpxxk6oUBUtTBcqyQgzxsVTpWvK4_Hm8ynNr6BJdNX7OOB1fxhQJ61sqeumspGqZ3GElM_2qop0Cj4pgvwbwPytG0GReMGV1oa0DDIANvnMWcyIPedBdtuGosHZHfdpG27La4o0V23G14B6V9GbOhfGAtILB_-tdNHZHs1RHZIZ3lem8dAZpfZE4_an34RoBs |
| linkProvider | Royal Society of Chemistry |
| openUrl | ctx_ver=Z39.88-2004&ctx_enc=info%3Aofi%2Fenc%3AUTF-8&rfr_id=info%3Asid%2Fsummon.serialssolutions.com&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.atitle=Expeditious+preparation+of+%CE%B2-+sec+-alkyl+vicinal+amino+alcohols+used+for+chiral+ligand+synthesis&rft.jtitle=Organic+%26+biomolecular+chemistry&rft.au=Huang%2C+Guoqi&rft.au=Wu%2C+Yu&rft.au=Gong%2C+Hegui&rft.au=Chen%2C+Yunrong&rft.date=2023-08-02&rft.eissn=1477-0539&rft_id=info:doi/10.1039%2Fd3ob00803g&rft_id=info%3Apmid%2F37462436&rft.externalDocID=37462436 |
| thumbnail_l | http://covers-cdn.summon.serialssolutions.com/index.aspx?isbn=/lc.gif&issn=1477-0520&client=summon |
| thumbnail_m | http://covers-cdn.summon.serialssolutions.com/index.aspx?isbn=/mc.gif&issn=1477-0520&client=summon |
| thumbnail_s | http://covers-cdn.summon.serialssolutions.com/index.aspx?isbn=/sc.gif&issn=1477-0520&client=summon |