Catalytic asymmetric synthesis of alpha- and beta-amino phosphonic acid derivatives
Catalytic asymmetric reactions provide one of the most powerful and economical synthetic approaches to a variety of enantiomerically enriched compounds. As being analogues of the corresponding alpha- and beta-amino acids, optically active alpha- and beta-amino phosphonic acid derivatives have found...
Saved in:
| Published in | Chemical Society reviews Vol. 35; no. 7; p. 630 |
|---|---|
| Main Author | |
| Format | Journal Article |
| Language | English |
| Published |
England
22.06.2006
|
| Subjects | |
| Online Access | Get more information |
Cover
Loading…
| Abstract | Catalytic asymmetric reactions provide one of the most powerful and economical synthetic approaches to a variety of enantiomerically enriched compounds. As being analogues of the corresponding alpha- and beta-amino acids, optically active alpha- and beta-amino phosphonic acid derivatives have found widespread use in medicinal chemistry and the pharmaceutical sciences. Using catalytic amounts of chiral materials, asymmetric synthesis of enantiomerically enriched alpha- and beta-amino phosphonates has been a subject of growing interest. This tutorial review contains a compilation of the catalytic asymmetric synthetic methods developed to date and highlights their utility for obtaining these target compounds. |
|---|---|
| AbstractList | Catalytic asymmetric reactions provide one of the most powerful and economical synthetic approaches to a variety of enantiomerically enriched compounds. As being analogues of the corresponding alpha- and beta-amino acids, optically active alpha- and beta-amino phosphonic acid derivatives have found widespread use in medicinal chemistry and the pharmaceutical sciences. Using catalytic amounts of chiral materials, asymmetric synthesis of enantiomerically enriched alpha- and beta-amino phosphonates has been a subject of growing interest. This tutorial review contains a compilation of the catalytic asymmetric synthetic methods developed to date and highlights their utility for obtaining these target compounds. |
| Author | Ma, Jun-An |
| Author_xml | – sequence: 1 givenname: Jun-An surname: Ma fullname: Ma, Jun-An email: majun_an68@tju.edu.cn organization: Department of Chemistry, Tianjin University, Tianjin, 300072, China. majun_an68@tju.edu.cn |
| BackLink | https://www.ncbi.nlm.nih.gov/pubmed/16791334$$D View this record in MEDLINE/PubMed |
| BookMark | eNo1j01LxDAYhHNYcT8U_AWSP1DN2zRJe5SirrDgQT0vb75oZJuWJi7031tRDw8zl5lhtmQVh-gIuQF2B4w391qAAsa6FdkwzmTBGJRrsk3pc3GgZHlJ1iBVA5xXG_LWYsbTnIOhmOa-d3labJpj7lwKiQ6e4mnssKAYLdUuY4F9iAMduyEtxJ-gCZZaN4Uz5nB26YpceDwld_2nO_Lx9Pje7ovD6_NL-3AozDKdC2d5WRmlBQpdN4LVzHhtvQQOrgJnKrXgLQr0iguphcQaS4bKo-BQQ7kjt7-945funT2OU-hxmo__78pvvf1RWw |
| CitedBy_id | crossref_primary_10_1021_acs_joc_0c00436 crossref_primary_10_1002_adsc_200800152 crossref_primary_10_1002_cjoc_201800262 crossref_primary_10_1002_adsc_200800277 crossref_primary_10_1016_j_tet_2018_10_058 crossref_primary_10_1007_s11434_009_3743_x crossref_primary_10_1021_ol203132h crossref_primary_10_1002_ejoc_202100581 crossref_primary_10_1039_B907303P crossref_primary_10_1002_adsc_201000792 crossref_primary_10_1002_asia_200800361 crossref_primary_10_1002_anie_200904779 crossref_primary_10_1002_cctc_202400817 crossref_primary_10_1002_adsc_201000038 crossref_primary_10_1039_C6QO00597G crossref_primary_10_1021_acs_joc_1c02024 crossref_primary_10_1038_s41467_017_02260_2 crossref_primary_10_1002_anie_202305315 crossref_primary_10_1016_j_tetasy_2010_07_017 crossref_primary_10_1021_acscentsci_3c00637 crossref_primary_10_1016_j_tetasy_2015_03_002 crossref_primary_10_1016_S1872_2067_17_62804_3 crossref_primary_10_1002_anie_201104912 crossref_primary_10_1002_ejoc_202400637 crossref_primary_10_1002_adsc_202200306 crossref_primary_10_1039_c3ra40958a crossref_primary_10_1039_C7DT02743E crossref_primary_10_1016_j_tetlet_2013_03_098 crossref_primary_10_1021_jo400798f crossref_primary_10_1002_asia_202000299 crossref_primary_10_1021_ol9000813 crossref_primary_10_1016_j_jfluchem_2014_07_008 crossref_primary_10_1016_j_tetasy_2007_04_021 crossref_primary_10_1002_ange_201308514 crossref_primary_10_1002_chem_200902634 crossref_primary_10_1002_ejic_202001170 crossref_primary_10_1002_ajoc_201402178 crossref_primary_10_1055_a_2329_4214 crossref_primary_10_1002_ejoc_201201589 crossref_primary_10_1039_b926037d crossref_primary_10_1039_C8QO01098F crossref_primary_10_1016_j_tetasy_2014_05_010 crossref_primary_10_1039_C6DT03712G crossref_primary_10_1039_D1OB02003J crossref_primary_10_1002_adsc_200800131 crossref_primary_10_1002_hc_20759 crossref_primary_10_1002_ajoc_201800604 crossref_primary_10_1002_aoc_6568 crossref_primary_10_1002_adsc_202300563 crossref_primary_10_1002_cctc_201300050 crossref_primary_10_1021_jacs_7b02324 crossref_primary_10_1021_jo9004958 crossref_primary_10_1002_adsc_201300224 crossref_primary_10_1039_c1cc14242a crossref_primary_10_6023_cjoc202405013 crossref_primary_10_1021_acs_orglett_0c01709 crossref_primary_10_1039_D2QO00184E crossref_primary_10_1002_adsc_201000611 crossref_primary_10_1039_D3SC04171A crossref_primary_10_1039_C9DT01237K crossref_primary_10_1002_anie_201308514 crossref_primary_10_1007_s11814_016_0098_2 crossref_primary_10_1016_j_tet_2019_04_010 crossref_primary_10_1039_c4cc01389a crossref_primary_10_1021_acs_orglett_6b01514 crossref_primary_10_1002_rcm_4938 crossref_primary_10_1016_j_jcou_2022_101939 crossref_primary_10_1021_acs_orglett_8b02707 crossref_primary_10_1002_chem_200901893 crossref_primary_10_1021_acs_joc_6b00326 crossref_primary_10_1021_acs_orglett_1c02750 crossref_primary_10_1002_tcr_201600129 crossref_primary_10_1021_jacs_4c04129 crossref_primary_10_1038_nprot_2012_108 crossref_primary_10_1002_ejoc_200800208 crossref_primary_10_1039_C6CC02463G crossref_primary_10_1016_j_tetasy_2009_12_022 crossref_primary_10_1016_j_tet_2010_09_026 crossref_primary_10_1016_j_tetasy_2008_04_019 crossref_primary_10_1016_j_tet_2011_11_054 crossref_primary_10_1039_C5QO00378D crossref_primary_10_1016_j_tet_2020_131896 crossref_primary_10_1016_j_tetasy_2008_10_010 crossref_primary_10_1038_s41467_019_11528_8 crossref_primary_10_1039_b617791n crossref_primary_10_1002_hc_21324 crossref_primary_10_1021_acs_orglett_6b02841 crossref_primary_10_1002_ange_201104912 crossref_primary_10_1002_chem_200802688 crossref_primary_10_1016_j_tetasy_2009_05_023 crossref_primary_10_1016_j_molstruc_2020_128193 crossref_primary_10_1039_D2OB01419J crossref_primary_10_1016_j_tetasy_2009_05_021 crossref_primary_10_1002_hlca_201100025 crossref_primary_10_1002_adsc_200700466 crossref_primary_10_1007_s00706_018_2303_y crossref_primary_10_1039_C4CC09477H crossref_primary_10_1039_C4RA04179H crossref_primary_10_1039_C7NJ03345A crossref_primary_10_1039_C5NJ00409H crossref_primary_10_1002_adsc_201600945 crossref_primary_10_1002_ejoc_201403184 crossref_primary_10_1021_acs_orglett_9b03800 crossref_primary_10_1039_b807027j crossref_primary_10_1002_cctc_201300089 crossref_primary_10_1002_ejoc_201700249 crossref_primary_10_1039_c0ob01059f crossref_primary_10_1016_j_tet_2013_10_001 crossref_primary_10_1039_C4CC10390D crossref_primary_10_1016_j_tet_2008_01_022 crossref_primary_10_1021_jo900300c crossref_primary_10_1021_acs_orglett_0c02229 crossref_primary_10_1021_ol3012666 crossref_primary_10_1021_ol4010118 crossref_primary_10_1002_ajoc_202400100 crossref_primary_10_1021_ct501147a crossref_primary_10_1039_C6OB00540C crossref_primary_10_1002_chem_200901901 crossref_primary_10_3390_molecules23061240 crossref_primary_10_1002_aoc_6594 crossref_primary_10_1021_jo1014917 crossref_primary_10_1039_C6CC04096A crossref_primary_10_1021_acs_joc_8b01048 crossref_primary_10_1002_ange_202305315 crossref_primary_10_1039_C5CC04826E crossref_primary_10_1016_j_tet_2014_06_013 crossref_primary_10_1016_j_molstruc_2020_127838 crossref_primary_10_1016_j_tet_2018_01_033 crossref_primary_10_1021_acs_inorgchem_8b02206 crossref_primary_10_1039_C8CC03017K crossref_primary_10_1021_acs_orglett_4c04380 crossref_primary_10_1021_ol100504h crossref_primary_10_1016_j_cclet_2016_01_046 crossref_primary_10_1039_C4OB01472C crossref_primary_10_1002_ange_200904779 crossref_primary_10_1002_ejoc_201101365 crossref_primary_10_1039_C9OB02649E crossref_primary_10_1021_acs_orglett_8b01422 crossref_primary_10_1016_j_ejmech_2007_08_010 crossref_primary_10_1002_asia_201200025 crossref_primary_10_1021_ol402059w crossref_primary_10_3390_molecules23040859 crossref_primary_10_1039_D4TA02396J crossref_primary_10_1002_cjoc_201300615 crossref_primary_10_1002_ejoc_201801610 crossref_primary_10_1039_D4OB00243A crossref_primary_10_1002_ajoc_201600431 crossref_primary_10_1039_D2QO01304E crossref_primary_10_1016_j_tetlet_2007_06_090 crossref_primary_10_1021_acs_inorgchem_6b02592 crossref_primary_10_1021_om801145v crossref_primary_10_1039_D4OB01212G crossref_primary_10_1002_adsc_201200574 crossref_primary_10_1016_j_mcat_2021_111396 crossref_primary_10_1002_hc_20704 crossref_primary_10_1021_jo502332r crossref_primary_10_1002_adsc_201300559 crossref_primary_10_1002_cjoc_201200119 crossref_primary_10_1002_ejoc_201001096 crossref_primary_10_1002_adsc_202001345 crossref_primary_10_1021_acscatal_8b05001 crossref_primary_10_1002_adsc_200900208 crossref_primary_10_1002_adsc_201100482 crossref_primary_10_1016_j_tet_2008_09_083 |
| ContentType | Journal Article |
| DBID | CGR CUY CVF ECM EIF NPM |
| DOI | 10.1039/b517100h |
| DatabaseName | Medline MEDLINE MEDLINE (Ovid) MEDLINE MEDLINE PubMed |
| DatabaseTitle | MEDLINE Medline Complete MEDLINE with Full Text PubMed MEDLINE (Ovid) |
| DatabaseTitleList | MEDLINE |
| 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: EIF name: MEDLINE url: https://proxy.k.utb.cz/login?url=https://www.webofscience.com/wos/medline/basic-search sourceTypes: Index Database |
| DeliveryMethod | no_fulltext_linktorsrc |
| Discipline | Chemistry |
| ExternalDocumentID | 16791334 |
| Genre | Research Support, Non-U.S. Gov't Journal Article Review |
| GroupedDBID | --- -DZ -JG -~X 0-7 0R~ 0UZ 186 1TJ 29B 2WC 3EH 4.4 53G 5GY 6J9 6TJ 705 70~ 71~ 7~J 85S 8WZ 9M8 A6W AAEMU AAHBH AAIWI AAJAE AAMEH AANOJ AAUTI AAWGC AAXHV AAXPP ABASK ABDPE ABDVN ABEMK ABJNI ABPDG ABRYZ ABXOH ACGFO ACGFS ACHDF ACIWK ACKIV ACLDK ACNCT ACPVT ACRPL ADMRA ADNMO ADSRN AEFDR AENEX AENGV AESAV AETIL AFFDN AFFNX AFLYV AFOGI AFRDS AFRZK AFVBQ AGEGJ AGKEF AGRSR AGSTE AHGCF AHGXI AI. AIDUJ ALMA_UNASSIGNED_HOLDINGS ALSGL ANBJS ANLMG ANUXI APEMP AQHUZ ASKNT ASPBG AUDPV AVWKF AZFZN BBWZM BLAPV BSQNT C6K CAG CGR COF CS3 CUY CVF DU5 EBS ECGLT ECM EE0 EEHRC EF- EIF EJD F5P FA8 FEDTE GGIMP GNO H13 HF~ HVGLF HZ~ H~9 H~N IDY IDZ J3G J3H J3I L-8 M4U MVM N9A NDZJH NPM O9- OK1 P2P R56 R7B R7D RAOCF RCLXC RCNCU RIG RNS ROL RPMJG RRA RRC RRXOS RSCEA SC5 SKA SKH SLH TN5 TWZ UPT UQL VH1 VH6 VXZ WH7 WHG XJT XOL YIN Z5M ZCG ZKB ~02 |
| ID | FETCH-LOGICAL-c334t-ed324c7b5a5b895080cfbdf6131e41ec47ec4fda5af7356b56a8a20a7fa531812 |
| ISSN | 0306-0012 |
| IngestDate | Wed Feb 19 01:45:57 EST 2025 |
| IsPeerReviewed | true |
| IsScholarly | true |
| Issue | 7 |
| Language | English |
| LinkModel | OpenURL |
| MergedId | FETCHMERGED-LOGICAL-c334t-ed324c7b5a5b895080cfbdf6131e41ec47ec4fda5af7356b56a8a20a7fa531812 |
| PMID | 16791334 |
| ParticipantIDs | pubmed_primary_16791334 |
| PublicationCentury | 2000 |
| PublicationDate | 2006-06-22 |
| PublicationDateYYYYMMDD | 2006-06-22 |
| PublicationDate_xml | – month: 06 year: 2006 text: 2006-06-22 day: 22 |
| PublicationDecade | 2000 |
| PublicationPlace | England |
| PublicationPlace_xml | – name: England |
| PublicationTitle | Chemical Society reviews |
| PublicationTitleAlternate | Chem Soc Rev |
| PublicationYear | 2006 |
| SSID | ssj0011762 |
| Score | 2.3218935 |
| SecondaryResourceType | review_article |
| Snippet | Catalytic asymmetric reactions provide one of the most powerful and economical synthetic approaches to a variety of enantiomerically enriched compounds. As... |
| SourceID | pubmed |
| SourceType | Index Database |
| StartPage | 630 |
| SubjectTerms | Catalysis Imines - chemistry Ligands Molecular Structure Organophosphonates - chemical synthesis Organophosphonates - chemistry Oxidation-Reduction Stereoisomerism |
| Title | Catalytic asymmetric synthesis of alpha- and beta-amino phosphonic acid derivatives |
| URI | https://www.ncbi.nlm.nih.gov/pubmed/16791334 |
| Volume | 35 |
| hasFullText | |
| inHoldings | 1 |
| isFullTextHit | |
| isPrint | |
| link | http://utb.summon.serialssolutions.com/2.0.0/link/0/eLvHCXMwnZ3PT8IwFMcb0YNejL9_mx68kerK1haOhGiIiV6EhBvpz8CBQQIxwb_e125jEzX-OLCQdixdP6N5r2_v-xC6MVSLyFJLnIqNDzMq0mJGk8RwqxyjXAclpqdn3u0njwM2KAveheyShbrVb1_mlfyHKrQBV58l-weyq4tCA3wHvnAEwnD8FeOO33tZBsnV-XIy8cWxtNcgAKMu1xkJqbQkRAiUXUgiJ-N0Wp-NpnP_Trr_oR6buoHBvgYF8HnVWF2JCRSvdubSpeUudpbXkZJ2ur57wEmjuqEY-7aIflgRMwGRnLyoLG88i6F8Wnaj2KuWKka9VtCoegpM2GwSpt_He8AhTn7uXRPALrpqqAaugK9t6jdk8kARFTwPFGW3UegLx627YjheFza_xJrvEGyI3h7azY1_3M5I7qMNmx6g7U5Rc-8QvayI4pIoXhHFU4czohiI4pIoLoliTxRXiB6h_sN9r9MledkLomGIC2INGLlaKCaZavoivZF2yjiwu6hNqNWJgI8zkkknYsYV47IpG5EUTsKCCgbbMdpMp6k9RdhEQplYSHAbwROUSlqRNFzLJYwqqrk9QyfZfAxnmbbJsJip8297LtBO-SBdoi0HfyZ7BZbZQl0HNu_0_Dmh |
| linkProvider | National Library of Medicine |
| 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=Catalytic+asymmetric+synthesis+of+alpha-+and+beta-amino+phosphonic+acid+derivatives&rft.jtitle=Chemical+Society+reviews&rft.au=Ma%2C+Jun-An&rft.date=2006-06-22&rft.issn=0306-0012&rft.volume=35&rft.issue=7&rft.spage=630&rft_id=info:doi/10.1039%2Fb517100h&rft_id=info%3Apmid%2F16791334&rft_id=info%3Apmid%2F16791334&rft.externalDocID=16791334 |
| thumbnail_l | http://covers-cdn.summon.serialssolutions.com/index.aspx?isbn=/lc.gif&issn=0306-0012&client=summon |
| thumbnail_m | http://covers-cdn.summon.serialssolutions.com/index.aspx?isbn=/mc.gif&issn=0306-0012&client=summon |
| thumbnail_s | http://covers-cdn.summon.serialssolutions.com/index.aspx?isbn=/sc.gif&issn=0306-0012&client=summon |