論文

査読有り
2017年

Direct Access to N-Unprotected α- and/or β-Tetrasubstituted Amino Acid Esters via Direct Catalytic Mannich-Type Reactions Using N-Unprotected Trifluoromethyl Ketimines

Chemistry - A European Journal
  • Sawa, M.
  • ,
  • Morisaki, K.
  • ,
  • Kondo, Y.
  • ,
  • Morimoto, H.
  • ,
  • Ohshima, T.

23
67
開始ページ
17022
終了ページ
17028
記述言語
掲載種別
研究論文(学術雑誌)
DOI
10.1002/chem.201703516

© 2017 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim Direct catalytic C−C bond-forming addition to N-unprotected ketimines is an efficient and straightforward method of synthesizing N-unprotected tetrasubstituted amines that eliminates prior protection/deprotection steps and allows facile transformation of the products. Despite its advantages, however, N-unprotected ketimines have difficulties in C−C bond-forming reactions, and only a limited number of reactions and substrates are reported compared with their N-protected counterparts. Herein we report that N-unprotected trifluoromethyl ketimines are effective for C−C bond-forming reactions using Mannich-type reactions as a model case. We demonstrate that Lewis acid catalysis was effective for promoting reactions with various N-unprotected trifluoromethyl ketimines, and thiourea organocatalysis was effective for promoting highly enantioselective reactions with various carbonyl nucleophiles, providing direct access to various N-unprotected α- and/or β-tetrasubstituted amino acid esters. Furthermore, direct construction of vicinal tetrasubstituted chiral carbon stereocenters was achieved for the first time in a highly enantio- and diastereoselective manner. These results demonstrate the potential of N-unprotected ketimines as substrates applicable to many other addition reactions.

Web of Science ® 被引用回数 : 31

リンク情報
DOI
https://doi.org/10.1002/chem.201703516
PubMed
https://www.ncbi.nlm.nih.gov/pubmed/28950035
Web of Science
https://gateway.webofknowledge.com/gateway/Gateway.cgi?GWVersion=2&SrcAuth=JSTA_CEL&SrcApp=J_Gate_JST&DestLinkType=FullRecord&KeyUT=WOS:000418570000017&DestApp=WOS_CPL
URL
http://www.scopus.com/inward/record.url?eid=2-s2.0-85035772279&partnerID=MN8TOARS
Scopus Citedby
https://www.scopus.com/inward/citedby.uri?partnerID=HzOxMe3b&scp=85035772279&origin=inward
ID情報
  • DOI : 10.1002/chem.201703516
  • ISSN : 0947-6539
  • eISSN : 1521-3765
  • ORCIDのPut Code : 54231878
  • PubMed ID : 28950035
  • SCOPUS ID : 85035772279
  • Web of Science ID : WOS:000418570000017

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