論文

査読有り
2017年

Direct enantioselective alkynylation of α-ketoesters and α-ketiminoesters catalyzed by [bis(oxazoline)phenyl]rhodium(III) complexes

Heterocycles
  • Morisaki, K.
  • ,
  • Morimoto, H.
  • ,
  • Mashima, K.
  • ,
  • Ohshima, T.

95
2
開始ページ
637
終了ページ
661
記述言語
英語
掲載種別
研究論文(学術雑誌)
DOI
10.3987/REV-16-SR(S)4
出版者・発行元
PERGAMON-ELSEVIER SCIENCE LTD

This review summarizes our studies of the direct enantioselective alkynylation of alpha-ketoesters and alpha-ketiminoesters catalyzed by [bis(oxazoline)phenyl]rhodium(M) aphebox)Rh(III)) complexes. The reactions provide chiral alpha-tetrasubstituted propargyl alcohols and propargylamines under proton-transfer conditions in high yield and with high enantioselectivity. The unique nature of (phebox)Rh(III) complexes allows the reactions to occur in the presence of various functional groups, including an electrophilic aldehyde functionality. Mechanistic studies revealed that the generation of (alkynyl)Rh(III) complexes limited the overall reactivity, which led us to use (trimethylsilylethynyl)(phebox)Rh(III) complexes as efficient pre-catalysts. The use of (trimethylsilylethynyl)(phebox)Rh(III) complexes reduced catalyst loading to as low as 0.5 mol%, and expanded the substrate scope to unprecedented alpha-ketiminophosphonate and cyclic N-sulfonyl alpha-ketiminoesters.

Web of Science ® 被引用回数 : 6

リンク情報
DOI
https://doi.org/10.3987/REV-16-SR(S)4
Web of Science
https://gateway.webofknowledge.com/gateway/Gateway.cgi?GWVersion=2&SrcAuth=JSTA_CEL&SrcApp=J_Gate_JST&DestLinkType=FullRecord&KeyUT=WOS:000403862700001&DestApp=WOS_CPL
URL
http://www.scopus.com/inward/record.url?eid=2-s2.0-85025700767&partnerID=MN8TOARS
ID情報
  • DOI : 10.3987/REV-16-SR(S)4
  • ISSN : 0385-5414
  • eISSN : 1881-0942
  • ORCIDのPut Code : 54231881
  • SCOPUS ID : 85025700767
  • Web of Science ID : WOS:000403862700001

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