Palladium-catalysed arylative cyclisation of N-allylacetamides with aryl halides yielding benzyl-substituted oxazolines
Treatment of N-allylacetamide with aryl halide in the presence of sodium t-butoxide and a palladium catalyst leads to arylative cyclisation to provide the corresponding benzyl-substituted oxazoline in high yield.
Saved in:
| Published in | Chemical communications (Cambridge, England) no. 38; pp. 5754 - 5756 |
|---|---|
| Main Authors | , , , |
| Format | Journal Article |
| Language | English |
| Published |
CAMBRIDGE
Royal Soc Chemistry
01.01.2009
|
| Subjects | |
| Online Access | Get full text |
| ISSN | 1359-7345 1364-548X 1364-548X |
| DOI | 10.1039/b912895f |
Cover
| Abstract | Treatment of N-allylacetamide with aryl halide in the presence of sodium t-butoxide and a palladium catalyst leads to arylative cyclisation to provide the corresponding benzyl-substituted oxazoline in high yield. |
|---|---|
| AbstractList | Treatment of N-allylacetamide with aryl halide in the presence of sodium t-butoxide and a palladium catalyst leads to arylative cyclisation to provide the corresponding benzyl-substituted oxazoline in high yield.Treatment of N-allylacetamide with aryl halide in the presence of sodium t-butoxide and a palladium catalyst leads to arylative cyclisation to provide the corresponding benzyl-substituted oxazoline in high yield. Treatment of N-allylacetamide with aryl halide in the presence of sodium t-butoxide and a palladium catalyst leads to arylative cyclisation to provide the corresponding benzyl-substituted oxazoline in high yield. |
| Author | Fujino, Daishi Oshima, Koichiro Yorimitsu, Hideki Hayashi, Sayuri |
| Author_xml | – sequence: 1 givenname: Daishi surname: Fujino fullname: Fujino, Daishi – sequence: 2 givenname: Sayuri surname: Hayashi fullname: Hayashi, Sayuri – sequence: 3 givenname: Hideki surname: Yorimitsu fullname: Yorimitsu, Hideki – sequence: 4 givenname: Koichiro surname: Oshima fullname: Oshima, Koichiro |
| BackLink | https://www.ncbi.nlm.nih.gov/pubmed/19774259$$D View this record in MEDLINE/PubMed |
| BookMark | eNqNksuKFTEQhoOMOBcFn0B6pyA9Jt3JSbKUgzcY1IWCuyaXihNJJ2MnPceepzfnMkdwIWaTIvX9RdWfOkcnMUVA6CnBlwT38pWWpBOSuQfojPQr2jIqvp1sYyZb3lN2is5z_oHrIUw8QqdEck47Js_Q5rMKQVk_j61RRYUlg23UtARV_C00ZjHB5xqn2CTXfGwrXXMGihq9hdxsfLne8c21CruXxUOwPn5vNMS7JbR51rn4MpdaOP1Sdyn4CPkxeuhUyPDkcF-gr2_ffFm_b68-vfuwfn3Vmtp7aakgDnfOWak70nWUKA1YcA7SWm21YlJoyQ0hrIcVI9xgp4QkWNZkX4X9BXq-r3szpZ8z5DKMPhuoM0dIcx6qO5hRJlglX_yT7PqeEUqF5BV9dkBnPYIdbiY_Vg-Ge1srIPbABnRy2XiIBo5Y_YaO423P22i19mVn8DrNsVTpy_-XVvpyT5sp5TyBG8yhWpmUDwPBw3ZBhvsF-TPlUXBs_m_0N3ySupo |
| CitedBy_id | crossref_primary_10_1021_ja5029028 crossref_primary_10_1002_chin_201008131 crossref_primary_10_1021_acs_orglett_1c02539 crossref_primary_10_1021_acs_joc_5b01227 crossref_primary_10_1016_j_tet_2011_07_087 crossref_primary_10_1021_acs_joc_3c02773 crossref_primary_10_1016_j_bmc_2013_07_019 crossref_primary_10_1021_jo501606c |
| Cites_doi | 10.1039/a806930a 10.1016/j.tetasy.2004.09.037 10.1016/j.tetlet.2005.11.148 10.1016/j.tet.2006.10.003 10.1016/S0040-4020(01)86953-2 10.1039/c39830001489 10.1021/ol061182q 10.1002/anie.200903178 10.1016/S0040-4039(00)96017-9 10.3987/COM-05-S(T)16 10.1002/ejoc.200600767 10.1021/ar50130a002 10.1016/S1367-5931(98)80027-6 10.1021/ar960062n 10.1002/adsc.200303178 10.1016/S0040-4039(98)00534-6 10.1021/ja054754v 10.1055/s-0028-1087339 10.1016/j.tet.2007.12.014 10.1039/b007741k 10.1039/b304142p 10.1021/jo050022+ 10.1016/S0957-4166(97)00593-4 10.1021/cr00064a005 10.1021/ja057489m 10.1021/cr60139a002 10.1021/jo991065r 10.1016/S0040-4020(01)82384-X 10.1021/ja0394838 10.1351/pac200880040743 10.1021/ol8002173 10.1021/cr60273a003 10.1002/anie.200701386 10.1002/adsc.200600516 |
| ContentType | Journal Article |
| DBID | AAYXX CITATION 17B 1KM 1KN BLEPL DTL EGQ GDOUO CGR CUY CVF ECM EIF NPM 7S9 L.6 7X8 |
| DOI | 10.1039/b912895f |
| DatabaseName | CrossRef Web of Knowledge Index Chemicus Current Chemical Reactions Web of Science Core Collection Science Citation Index Expanded Web of Science Primary (SCIE, SSCI & AHCI) Web of Science - Science Citation Index Expanded - 2009 Medline MEDLINE MEDLINE (Ovid) MEDLINE MEDLINE PubMed AGRICOLA AGRICOLA - Academic MEDLINE - Academic |
| DatabaseTitle | CrossRef Web of Science MEDLINE Medline Complete MEDLINE with Full Text PubMed MEDLINE (Ovid) AGRICOLA AGRICOLA - Academic MEDLINE - Academic |
| DatabaseTitleList | MEDLINE - Academic MEDLINE AGRICOLA Web of Science |
| 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 | 1364-548X |
| EndPage | 5756 |
| ExternalDocumentID | 19774259 000270115300026 10_1039_b912895f |
| Genre | Research Support, Non-U.S. Gov't Journal Article |
| GrantInformation_xml | – fundername: MEXT; Ministry of Education, Culture, Sports, Science and Technology, Japan (MEXT) – fundername: JSPS; Ministry of Education, Culture, Sports, Science and Technology, Japan (MEXT); Japan Society for the Promotion of Science – fundername: Eisai and Kyoto University; Eisai Co Ltd |
| GroupedDBID | --- -DZ -~X 0-7 0R~ 0UZ 186 1TJ 29B 2WC 3EH 4.4 53G 5GY 6J9 6TJ 705 70~ 71~ 7~J 9M8 AAEMU AAHBH AAIWI AAJAE AAMEH AANOJ AAWGC AAXHV AAXPP AAYOK AAYXX ABASK ABDVN ABEMK ABJNI ABPDG ABRYZ ABXOH ACBEA ACGFO ACGFS ACHDF ACIWK ACLDK ACNCT ACRPL ADMRA ADNMO ADSRN ADXHL AEFDR AENEX AENGV AESAV AETIL AFFNX AFLYV AFOGI AFRDS AFRZK AFVBQ AGEGJ AGKEF AGQPQ AGRSR AHGCF AHGXI AI. AKMSF ALMA_UNASSIGNED_HOLDINGS ALSGL ALUYA ANBJS ANLMG ANUXI APEMP AQHUZ ASKNT ASPBG AUDPV AVWKF AZFZN BBWZM BLAPV BSQNT C6K CAG CITATION COF CS3 DU5 EBS ECGLT EE0 EEHRC EF- EJD F5P FA8 FEDTE GGIMP GNO H13 HVGLF HZ~ H~N IDY IDZ IH2 J3G J3H J3I L-8 M4U MVM N9A NDZJH O9- OHT P2P R56 R7B R7C R7D RAOCF RCLXC RCNCU RIG RNS ROL RPMJG RRA RRC RRXOS RSCEA SJN SKA SKF SKH SLH TN5 TWZ UHB UPT VH1 VH6 WH7 WHG X7L XJT ZCG ZKB 17B 1KM 1KN BLEPL DTL GROUPED_WOS_SCIENCE_CITATION_INDEX_EXPANDED GROUPED_WOS_WEB_OF_SCIENCE -JG AGSTE CGR CUY CVF ECM EIF NPM VQA VXZ 7S9 L.6 7X8 |
| ID | FETCH-LOGICAL-c359t-481f02ffd9b212241abe0877e9ddbdba598b97c1153e6517c0fa89109bdb302f3 |
| ISICitedReferencesCount | 8 |
| ISICitedReferencesURI | https://gateway.webofknowledge.com/gateway/Gateway.cgi?GWVersion=2&SrcApp=Summon&SrcAuth=ProQuest&DestApp=WOS&DestLinkType=CitingArticles&UT=000270115300026 |
| ISSN | 1359-7345 1364-548X |
| IngestDate | Thu Jul 10 16:41:45 EDT 2025 Fri Jul 11 15:39:41 EDT 2025 Wed Feb 19 01:56:25 EST 2025 Sat Sep 06 04:35:33 EDT 2025 Fri May 30 07:56:51 EDT 2025 Tue Jul 01 01:17:45 EDT 2025 Thu Apr 24 23:05:49 EDT 2025 |
| IsDoiOpenAccess | false |
| IsOpenAccess | true |
| IsPeerReviewed | true |
| IsScholarly | true |
| Issue | 38 |
| Keywords | CARBOAMINATION REACTIONS ALKENES ISOXAZOLIDINES ASYMMETRIC-SYNTHESIS ACID TETRAHYDROFURANS ONE-POT SYNTHESIS CARBOETHERIFICATION THIAZOLE STEREOSELECTIVE-SYNTHESIS |
| Language | English |
| LinkModel | OpenURL |
| LogoURL | https://exlibris-pub.s3.amazonaws.com/fromwos-v2.jpg |
| MergedId | FETCHMERGED-LOGICAL-c359t-481f02ffd9b212241abe0877e9ddbdba598b97c1153e6517c0fa89109bdb302f3 |
| Notes | ObjectType-Article-1 SourceType-Scholarly Journals-1 ObjectType-Feature-2 content type line 23 |
| ORCID | 0000-0002-0153-1888 |
| OpenAccessLink | http://hdl.handle.net/2433/86179 |
| PMID | 19774259 |
| PQID | 2335144897 |
| PQPubID | 24069 |
| PageCount | 3 |
| ParticipantIDs | pubmed_primary_19774259 crossref_primary_10_1039_b912895f webofscience_primary_000270115300026CitationCount proquest_miscellaneous_2335144897 webofscience_primary_000270115300026 crossref_citationtrail_10_1039_b912895f proquest_miscellaneous_734054585 |
| ProviderPackageCode | CITATION AAYXX |
| PublicationCentury | 2000 |
| PublicationDate | 2009-01-01 |
| PublicationDateYYYYMMDD | 2009-01-01 |
| PublicationDate_xml | – month: 01 year: 2009 text: 2009-01-01 day: 01 |
| PublicationDecade | 2000 |
| PublicationPlace | CAMBRIDGE |
| PublicationPlace_xml | – name: CAMBRIDGE – name: England |
| PublicationTitle | Chemical communications (Cambridge, England) |
| PublicationTitleAbbrev | CHEM COMMUN |
| PublicationTitleAlternate | Chem Commun (Camb) |
| PublicationYear | 2009 |
| Publisher | Royal Soc Chemistry |
| Publisher_xml | – name: Royal Soc Chemistry |
| References | Tiecco (b912895f-(cit4b)/*[position()=1]) 1993; 49 Johnson (b912895f-(cit3b)/*[position()=1]) 2000; 33 Cook (b912895f-(cit6b)/*[position()=1]) 1998; 39 Bergeron (b912895f-(cit1a)/*[position()=1]) 1984; 84 Morino (b912895f-(cit4e)/*[position()=1]) 2006; 62 Nakhla (b912895f-(cit8a)/*[position()=1]) 2006; 128 Hay (b912895f-(cit8b)/*[position()=1]) 2005; 127 Cardillo (b912895f-(cit4c)/*[position()=1]) 1983 Lewis (b912895f-(cit1c)/*[position()=1]) 2002; 19 Lee (b912895f-(cit6a)/*[position()=1]) 1999; 64 Jiang (b912895f-(cit8e)/*[position()=1]) 2008; 10 Frump (b912895f-(cit2b)/*[position()=1]) 1971; 71 Ghosh (b912895f-(cit3a)/*[position()=1]) 1998; 9 Wolfe (b912895f-(cit8i)/*[position()=1]) 2007 Jiang (b912895f-(cit8h)/*[position()=1]) 2008; 64 Gant (b912895f-(cit2c)/*[position()=1]) 1994; 50 Roy (b912895f-(cit1b)/*[position()=1]) 1999; 16 Meyers (b912895f-(cit2d)/*[position()=1]) 1978; 11 Wiley (b912895f-(cit2a)/*[position()=1]) 1949; 44 Hay (b912895f-(cit8g)/*[position()=1]) 2007; 46 Wolfe (b912895f-(cit8d)/*[position()=1]) 2004; 126 Abd El Samii (b912895f-(cit4a)/*[position()=1]) 1987; 28 Dongol (b912895f-(cit8f)/*[position()=1]) 2006; 47 Minakata (b912895f-(cit4d)/*[position()=1]) 2006; 8 Hay (b912895f-(cit8c)/*[position()=1]) 2005; 70 Hayashi (b912895f-(cit5)/*[position()=1]) 2009; 48 Langlois (b912895f-(cit2e)/*[position()=1]) 1998; 2 Nishiyama (b912895f-(cit3c)/*[position()=1]) 2008; 80 Kato (b912895f-(cit4f)/*[position()=1]) 2004; 15 Jin (b912895f-(cit1d)/*[position()=1]) 2003; 20 Braun (b912895f-(cit12)/*[position()=1]) 2004; 346 Cook (b912895f-(cit7)/*[position()=2]) 2006; 67 Wolfe (b912895f-(cit8j)/*[position()=1]) 2008 Benfatti (b912895f-(cit13)/*[position()=1]) 2007; 349 Wolfe, JP (WOS:000262108300002) 2008 Jiang, D (WOS:000255311200007) 2008; 10 Wolfe, JP (WOS:000243891700001) 2007; 2007 Cook, GR (WOS:000073490400013) 1998; 39 FRUMP, JA (WOS:A1971K405400003) 1971; 71 Ghosh, AK (WOS:000071895400001) 1998; 9 Wolfe, JP (WOS:000188926600016) 2004; 126 Braun, M (WOS:000221004500013) 2004; 346 Hay, MB (WOS:000249296900021) 2007; 46 Johnson, JS (WOS:000087894400003) 2000; 33 Cook, GR (WOS:000234988300019) 2006; 67 Hayashi, S (WOS:000269979100019) 2009; 48 Hay, MB (WOS:000228367100024) 2005; 70 Jin, Z (WOS:000187495000004) 2003; 20 Roy, RS (WOS:000079802400009) 1999; 16 Morino, Y (WOS:000242639200012) 2006; 62 Lewis, JR (WOS:000175145300005) 2002; 19 Minakata, S (WOS:000239001500045) 2006; 8 Jiang, DH (WOS:000253620600006) 2008; 64 BERGERON, RJ (WOS:A1984TZ48200005) 1984; 84 Lee, KY (WOS:000084600100015) 1999; 64 Nakhla, JS (WOS:000235942000040) 2006; 128 CARDILLO, G (WOS:A1983RV85000014) 1983 ABDELSAMII ZKM (WOS:000270115300026.1) 1987; 28 TIECCO, M (WOS:A1993LH48600014) 1993; 49 GANT, TG (WOS:A1994MW95800001) 1994; 50 Benfatti, F (WOS:000246990200031) 2007; 349 Kato, T (WOS:000225622900002) 2004; 15 MEYERS, AI (WOS:A1978FS52700002) 1978; 11 Langlois, Y (WOS:000071248800002) 1998; 2 Dongol, KG (WOS:000234953300017) 2006; 47 Nishiyama, H (WOS:000256291500009) 2008; 80 WILEY, RH (WOS:A1949UE86400002) 1949; 44 Hay, MB (WOS:000233617900044) 2005; 127 |
| References_xml | – volume: 16 start-page: 249 year: 1999 ident: b912895f-(cit1b)/*[position()=1] publication-title: Nat. Prod. Rep. doi: 10.1039/a806930a – volume: 15 start-page: 3693 year: 2004 ident: b912895f-(cit4f)/*[position()=1] publication-title: Tetrahedron: Asymmetry doi: 10.1016/j.tetasy.2004.09.037 – volume: 47 start-page: 927 year: 2006 ident: b912895f-(cit8f)/*[position()=1] publication-title: Tetrahedron Lett. doi: 10.1016/j.tetlet.2005.11.148 – volume: 62 start-page: 12247 year: 2006 ident: b912895f-(cit4e)/*[position()=1] publication-title: Tetrahedron doi: 10.1016/j.tet.2006.10.003 – volume: 50 start-page: 2297 year: 1994 ident: b912895f-(cit2c)/*[position()=1] publication-title: Tetrahedron doi: 10.1016/S0040-4020(01)86953-2 – start-page: 1489 year: 1983 ident: b912895f-(cit4c)/*[position()=1] publication-title: J. Chem. Soc., Chem. Commun. doi: 10.1039/c39830001489 – volume: 8 start-page: 3335 year: 2006 ident: b912895f-(cit4d)/*[position()=1] publication-title: Org. Lett. doi: 10.1021/ol061182q – volume: 48 year: 2009 ident: b912895f-(cit5)/*[position()=1] publication-title: Angew. Chem., Int. Ed. doi: 10.1002/anie.200903178 – volume: 28 start-page: 1949 year: 1987 ident: b912895f-(cit4a)/*[position()=1] publication-title: Tetrahedron Lett. doi: 10.1016/S0040-4039(00)96017-9 – volume: 67 start-page: 215 year: 2006 ident: b912895f-(cit7)/*[position()=2] publication-title: Heterocycles doi: 10.3987/COM-05-S(T)16 – start-page: 571 year: 2007 ident: b912895f-(cit8i)/*[position()=1] publication-title: Eur. J. Org. Chem. doi: 10.1002/ejoc.200600767 – volume: 11 start-page: 375 year: 1978 ident: b912895f-(cit2d)/*[position()=1] publication-title: Acc. Chem. Res. doi: 10.1021/ar50130a002 – volume: 2 start-page: 1 year: 1998 ident: b912895f-(cit2e)/*[position()=1] publication-title: Curr. Org. Chem. doi: 10.1016/S1367-5931(98)80027-6 – volume: 33 start-page: 325 year: 2000 ident: b912895f-(cit3b)/*[position()=1] publication-title: Acc. Chem. Res. doi: 10.1021/ar960062n – volume: 346 start-page: 474 year: 2004 ident: b912895f-(cit12)/*[position()=1] publication-title: Adv. Synth. Catal. doi: 10.1002/adsc.200303178 – volume: 39 start-page: 3405 year: 1998 ident: b912895f-(cit6b)/*[position()=1] publication-title: Tetrahedron Lett. doi: 10.1016/S0040-4039(98)00534-6 – volume: 127 start-page: 16468 year: 2005 ident: b912895f-(cit8b)/*[position()=1] publication-title: J. Am. Chem. Soc. doi: 10.1021/ja054754v – start-page: 2913 year: 2008 ident: b912895f-(cit8j)/*[position()=1] publication-title: Synlett doi: 10.1055/s-0028-1087339 – volume: 64 start-page: 1641 year: 2008 ident: b912895f-(cit8h)/*[position()=1] publication-title: Tetrahedron doi: 10.1016/j.tet.2007.12.014 – volume: 19 start-page: 223 year: 2002 ident: b912895f-(cit1c)/*[position()=1] publication-title: Nat. Prod. Rep. doi: 10.1039/b007741k – volume: 20 start-page: 584 year: 2003 ident: b912895f-(cit1d)/*[position()=1] publication-title: Nat. Prod. Rep. doi: 10.1039/b304142p – volume: 70 start-page: 3099 year: 2005 ident: b912895f-(cit8c)/*[position()=1] publication-title: J. Org. Chem. doi: 10.1021/jo050022+ – volume: 9 start-page: 1 year: 1998 ident: b912895f-(cit3a)/*[position()=1] publication-title: Tetrahedron: Asymmetry doi: 10.1016/S0957-4166(97)00593-4 – volume: 84 start-page: 587 year: 1984 ident: b912895f-(cit1a)/*[position()=1] publication-title: Chem. Rev. doi: 10.1021/cr00064a005 – volume: 128 start-page: 2893 year: 2006 ident: b912895f-(cit8a)/*[position()=1] publication-title: J. Am. Chem. Soc. doi: 10.1021/ja057489m – volume: 44 start-page: 447 year: 1949 ident: b912895f-(cit2a)/*[position()=1] publication-title: Chem. Rev. doi: 10.1021/cr60139a002 – volume: 64 start-page: 9450 year: 1999 ident: b912895f-(cit6a)/*[position()=1] publication-title: J. Org. Chem. doi: 10.1021/jo991065r – volume: 49 start-page: 5351 year: 1993 ident: b912895f-(cit4b)/*[position()=1] publication-title: Tetrahedron doi: 10.1016/S0040-4020(01)82384-X – volume: 126 start-page: 1620 year: 2004 ident: b912895f-(cit8d)/*[position()=1] publication-title: J. Am. Chem. Soc. doi: 10.1021/ja0394838 – volume: 80 start-page: 743 year: 2008 ident: b912895f-(cit3c)/*[position()=1] publication-title: Pure Appl. Chem. doi: 10.1351/pac200880040743 – volume: 10 start-page: 1695 year: 2008 ident: b912895f-(cit8e)/*[position()=1] publication-title: Org. Lett. doi: 10.1021/ol8002173 – volume: 71 start-page: 483 year: 1971 ident: b912895f-(cit2b)/*[position()=1] publication-title: Chem. Rev. doi: 10.1021/cr60273a003 – volume: 46 start-page: 6492 year: 2007 ident: b912895f-(cit8g)/*[position()=1] publication-title: Angew. Chem., Int. Ed. doi: 10.1002/anie.200701386 – volume: 349 start-page: 1256 year: 2007 ident: b912895f-(cit13)/*[position()=1] publication-title: Adv. Synth. Catal. doi: 10.1002/adsc.200600516 – volume: 128 start-page: 2893 year: 2006 ident: WOS:000235942000040 article-title: Intramolecular Pd-catalyzed carboetherification and carboamination. Influence of catalyst structure on reaction mechanism and product stereochemistry publication-title: JOURNAL OF THE AMERICAN CHEMICAL SOCIETY doi: 10.1021/ja057489m – volume: 28 start-page: 1949 year: 1987 ident: WOS:000270115300026.1 publication-title: TETRAHEDRON LETT – volume: 84 start-page: 587 year: 1984 ident: WOS:A1984TZ48200005 article-title: SYNTHESIS AND SOLUTION STRUCTURE OF MICROBIAL SIDEROPHORES publication-title: CHEMICAL REVIEWS – volume: 71 start-page: 483 year: 1971 ident: WOS:A1971K405400003 article-title: OXAZOLINES - THEIR PREPARATION, REACTIONS, AND APPLICATIONS publication-title: CHEMICAL REVIEWS – volume: 64 start-page: 9450 year: 1999 ident: WOS:000084600100015 article-title: Stereoselective intramolecular cyclization of allyl and homoallyl benzamide via π-allylpalladium complex catalyzed by Pd(0) publication-title: JOURNAL OF ORGANIC CHEMISTRY – volume: 50 start-page: 2297 year: 1994 ident: WOS:A1994MW95800001 article-title: THE CHEMISTRY OF 2-OXAZOLINES (1985-PRESENT) publication-title: TETRAHEDRON – volume: 47 start-page: 927 year: 2006 ident: WOS:000234953300017 article-title: Palladium(0)-catalyzed cascade one-pot synthesis of isoxazolidines publication-title: TETRAHEDRON LETTERS doi: 10.1016/j.tetlet.2005.11.148 – start-page: 1489 year: 1983 ident: WOS:A1983RV85000014 article-title: A NEW SYNTHETIC APPROACH TO 3-AMINO-1,2-DIOLS FROM ALLYLIC ALCOHOLS VIA TRICHLOROACETIMIDATES publication-title: JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS – volume: 349 start-page: 1256 year: 2007 ident: WOS:000246990200031 article-title: A microwave-enhanced, Lewis acid-catalyzed synthesis of 1,3-dioxolanes and oxazolines from epoxides publication-title: ADVANCED SYNTHESIS & CATALYSIS doi: 10.1002/adsc.200600516 – volume: 20 start-page: 584 year: 2003 ident: WOS:000187495000004 article-title: Muscarine, imidazole, oxazole, and thiazole alkaloids publication-title: NATURAL PRODUCT REPORTS doi: 10.1039/b304142p – start-page: 2913 year: 2008 ident: WOS:000262108300002 article-title: Stereoselective Synthesis of Saturated Heterocycles via Palladium-Catalyzed Alkene Carboetherification and Carboamination Reactions publication-title: SYNLETT doi: 10.1055/s-0028-1087339 – volume: 44 start-page: 447 year: 1949 ident: WOS:A1949UE86400002 article-title: THE CHEMISTRY OF THE OXAZOLINES publication-title: CHEMICAL REVIEWS – volume: 9 start-page: 1 year: 1998 ident: WOS:000071895400001 article-title: C2-symmetric chiral bis(oxazoline)-metal complexes in catalytic asymmetric synthesis publication-title: TETRAHEDRON-ASYMMETRY – volume: 15 start-page: 3693 year: 2004 ident: WOS:000225622900002 article-title: Development of a novel chiral spiro ligand bearing oxazoline publication-title: TETRAHEDRON-ASYMMETRY doi: 10.1016/j.tetasy.2004.09.037 – volume: 11 start-page: 375 year: 1978 ident: WOS:A1978FS52700002 article-title: ASYMMETRIC CARBON-CARBON BOND FORMATION FROM CHIRAL OXAZOLINES publication-title: ACCOUNTS OF CHEMICAL RESEARCH – volume: 80 start-page: 743 year: 2008 ident: WOS:000256291500009 article-title: Chiral phenyl-bis(oxazoline) as an efficient auxiliary for asymmetric catalysis publication-title: PURE AND APPLIED CHEMISTRY doi: 10.1351/pac200880040743 – volume: 39 start-page: 3405 year: 1998 ident: WOS:000073490400013 article-title: Palladium-catalyzed formation and stereoselective isomerization of 5-vinyloxazolines. Application to the formal synthesis of (S,S)-4-amino-3-hydroxy-5-phenylpentanoic acid publication-title: TETRAHEDRON LETTERS – volume: 19 start-page: 223 year: 2002 ident: WOS:000175145300005 article-title: Amaryllidaceae, Sceletium, imidazole, oxazole, thiazole, peptide and miscellaneous alkaloids publication-title: NATURAL PRODUCT REPORTS doi: 10.1039/b007741k – volume: 70 start-page: 3099 year: 2005 ident: WOS:000228367100024 article-title: Palladium-catalyzed synthesis of tetrahydrofurans from γ-hydroxy terminal alkenes:: Scope, limitations, and stereoselectivity publication-title: JOURNAL OF ORGANIC CHEMISTRY doi: 10.1021/jo050022+ – volume: 126 start-page: 1620 year: 2004 ident: WOS:000188926600016 article-title: Stereoselective synthesis of tetrahydrofurans via the palladium-catalyzed reaction of aryl bromides with γ-hydroxy alkenes:: Evidence for an unusual intramolecular olefin insertion into a Pd(Ar)(OR) intermediate publication-title: JOURNAL OF THE AMERICAN CHEMICAL SOCIETY doi: 10.1021/ja0394838 – volume: 16 start-page: 249 year: 1999 ident: WOS:000079802400009 article-title: Thiazole and oxazole peptides: biosynthesis and molecular machinery publication-title: NATURAL PRODUCT REPORTS – volume: 2 start-page: 1 year: 1998 ident: WOS:000071248800002 article-title: New uses of oxazolines, oxazoline N-oxides and dioxolanyliums in asymmetric synthesis publication-title: CURRENT ORGANIC CHEMISTRY – volume: 64 start-page: 1641 year: 2008 ident: WOS:000253620600006 article-title: Palladium-catalyzed cascade one-pot synthesis of 5-arylmethylisoxazolidines from N-homoallylhydroxylamines with aryl bromides publication-title: TETRAHEDRON doi: 10.1016/j.tet.2007.12.014 – volume: 48 start-page: 7224 year: 2009 ident: WOS:000269979100019 article-title: Synthesis of Aziridines by Palladium-Catalyzed Reactions of Allylamines with Aryl and Alkenyl Halides: Evidence of a syn-Carboamination Pathway publication-title: ANGEWANDTE CHEMIE-INTERNATIONAL EDITION doi: 10.1002/anie.200903178 – volume: 127 start-page: 16468 year: 2005 ident: WOS:000233617900044 article-title: Palladium-catalyzed synthesis of 2,1′-disubstituted tetrahydrofurans from γ-hydroxy internal alkenes.: Evidence for alkene insertion into a Pd-O bond and stereochemical scrambling via β-hydride elimination publication-title: JOURNAL OF THE AMERICAN CHEMICAL SOCIETY doi: 10.1021/ja054754v – volume: 46 start-page: 6492 year: 2007 ident: WOS:000249296900021 article-title: Stereoselective synthesis of isoxazolidines through pd-catalyzed carboetherification of N-butenylhydroxylamines publication-title: ANGEWANDTE CHEMIE-INTERNATIONAL EDITION doi: 10.1002/anie.200701386 – volume: 10 start-page: 1695 year: 2008 ident: WOS:000255311200007 article-title: Pd-catalyzed carboetherification of β,γ-unsaturated oximes:: A novel approach to Δ2-isoxazolines publication-title: ORGANIC LETTERS doi: 10.1021/ol8002173 – volume: 2007 start-page: 571 year: 2007 ident: WOS:000243891700001 article-title: Palladium-catalyzed carboetherification and carboamination reactions of γ-hydroxy- and γ-aminoalkenes for the synthesis of tetrahydrofurans and pyrrolidines publication-title: EUROPEAN JOURNAL OF ORGANIC CHEMISTRY doi: 10.1002/ejoc.200600767 – volume: 33 start-page: 325 year: 2000 ident: WOS:000087894400003 article-title: Chiral bis(oxazoline) copper(II) complexes: Versatile catalysts for enantioselective cycloaddition, aldol, Michael, and carbonyl ene reactions publication-title: ACCOUNTS OF CHEMICAL RESEARCH – volume: 49 start-page: 5351 year: 1993 ident: WOS:A1993LH48600014 article-title: ACETOXY LACTONIZATION OF ALKENYL ACETIC-ACIDS PROMOTED BY AMMONIUM PERSULFATE AND TRIFLUOROMETHANESULFONIC ACID IN ACETIC-ACID publication-title: TETRAHEDRON – volume: 67 start-page: 215 year: 2006 ident: WOS:000234988300019 article-title: Tandem palladium-catalyzed allene arylation and oxazoline formation publication-title: HETEROCYCLES – volume: 62 start-page: 12247 year: 2006 ident: WOS:000242639200012 article-title: Electrophilic cyclization of N-alkenylamides using a chloramine-T/I2 system publication-title: TETRAHEDRON doi: 10.1016/j.tet.2006.10.003 – volume: 346 start-page: 474 year: 2004 ident: WOS:000221004500013 article-title: The regioisomeric triphenylaminoethanols - Comparison of their efficiency in enantioselective catalysis publication-title: ADVANCED SYNTHESIS & CATALYSIS doi: 10.1002/adsc.200303178 – volume: 8 start-page: 3335 year: 2006 ident: WOS:000239001500045 article-title: Practical and convenient synthesis of N-heterocycles:: Stereoselective cyclization of N-alkenylamides with t-BuOI under neutral conditions publication-title: ORGANIC LETTERS doi: 10.1021/ol061182q |
| SSID | ssj0000158 |
| Score | 1.9778169 |
| Snippet | Treatment of N-allylacetamide with aryl halide in the presence of sodium t-butoxide and a palladium catalyst leads to arylative cyclisation to provide the... |
| Source | Web of Science |
| SourceID | proquest pubmed webofscience crossref |
| SourceType | Aggregation Database Index Database Enrichment Source |
| StartPage | 5754 |
| SubjectTerms | Acetamides - chemistry Catalysis catalysts catalytic activity chemical communication chemical reactions Chemistry Chemistry, Multidisciplinary Cyclization organic halogen compounds Oxazoles - chemical synthesis Oxazoles - chemistry palladium Palladium - chemistry Physical Sciences Science & Technology sodium Stereoisomerism |
| Title | Palladium-catalysed arylative cyclisation of N-allylacetamides with aryl halides yielding benzyl-substituted oxazolines |
| URI | http://gateway.webofknowledge.com/gateway/Gateway.cgi?GWVersion=2&SrcApp=Summon&SrcAuth=ProQuest&DestApp=WOS&DestLinkType=FullRecord&UT=000270115300026 https://www.ncbi.nlm.nih.gov/pubmed/19774259 https://www.proquest.com/docview/2335144897 https://www.proquest.com/docview/734054585 |
| WOS | 000270115300026 |
| WOSCitedRecordID | wos000270115300026 |
| hasFullText | 1 |
| inHoldings | 1 |
| isFullTextHit | |
| isPrint | |
| link | http://utb.summon.serialssolutions.com/2.0.0/link/0/eLvHCXMwnV1Zj9MwELbK7gO8IG7CJSOtxMMqS5vbj6tqVwvikuhKfatsxxGBtlm1iSD9wfwOZmwnTQ-kwkuUOJPL88Uej8ffEHISiFRy7sHoJJCRC-ONzBVMwO_OVJKJVCSpnj3_-Cm6ug7ej8Nxr_e7E7VUleJMrvauK_kfrUIZ6BVXyf6DZtubQgHsg35hCxqG7UE6_oJe8DSvZq72wtRLsB75op4aMm9Zy6kN1tF-AReka_Sal3yWp6pZ1wbymFFFl9QYz4bOA6Hmq3rqLqFZMbEE6Wnxi68ww48NOmzYDRrCAdldaaJdue1yMN3emmQhHcfDZfU913m_AXnoCFu3hTUmeDLu6rpa5OuGCVOQlctKd5fwvj_aU5_hgplZ3Fbk8lu-KDa8GWzLm2F8Jl8LeTps8t11Gmc_ZG7sG_rJM2XLosCFUde4g1VDF2NbZDBHg07vDofR3p6j7yPxqmDQX7Mw64qAzm9mGkEDNJY9y2C-Qd291aW2gY56Zhetbh_3olvk2ItjDCc4Pr8YvfvQITrTmWTbL2xokn32tnklTW9rnr9pQ-0MjPbaUNpeGt0jd-1Ah54b1N4nPTV_QG639f2Q_NyDXtqil3bQS4uM7qCXInq1PLXopQ166S566Rq9j8j15cVoeOXaNCCuhOoo3SAZZH0vy1ImPD0PzIVCGkvF0hRaEx6yRLBYYiWrKBzEsp_xBKxgBid9uNB_TI7mxVw9JTSCmuSKBX4WRWC5JiKNGBOB6HMuQpH1HfKmqdiJtBz5mKplOtGxGj6bNNpwyOtW8sbwwuyTaXQzgbrFmTg-V0W1nHg-LqAJEhY7hP5FBmDQx1nt0CFPjF7XD7I4cMhJV9Ht-S3UOWRwiNjQfjCSYZTPDrv1c3Jn_Re_IEflolIvwUovxSsL8T_4ve0E |
| 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=Palladium-catalysed+arylative+cyclisation+of+N-allylacetamides+with+aryl+halides+yielding+benzyl-substituted+oxazolines&rft.jtitle=Chemical+communications+%28Cambridge%2C+England%29&rft.au=Fujino%2C+Daishi&rft.au=Hayashi%2C+Sayuri&rft.au=Yorimitsu%2C+Hideki&rft.au=Oshima%2C+Koichiro&rft.date=2009-01-01&rft.pub=Royal+Soc+Chemistry&rft.issn=1359-7345&rft.eissn=1364-548X&rft.issue=38&rft.spage=5754&rft.epage=5756&rft_id=info:doi/10.1039%2Fb912895f&rft_id=info%3Apmid%2F19774259&rft.externalDBID=n%2Fa&rft.externalDocID=000270115300026 |
| thumbnail_l | http://covers-cdn.summon.serialssolutions.com/index.aspx?isbn=/lc.gif&issn=1359-7345&client=summon |
| thumbnail_m | http://covers-cdn.summon.serialssolutions.com/index.aspx?isbn=/mc.gif&issn=1359-7345&client=summon |
| thumbnail_s | http://covers-cdn.summon.serialssolutions.com/index.aspx?isbn=/sc.gif&issn=1359-7345&client=summon |