Chiral Nanoparticles/Lewis Acids as Cooperative Catalysts for Asymmetric 1,4-Addition of Arylboronic Acids to α,β-Unsaturated Amides

Tomohiro Yasukawa, Yuuki Saito, Hiroyuki Miyamura, Shū Kobayashi

Research output: Contribution to journalArticleResearchpeer-review

50 Citations (Scopus)

Abstract

Cooperative catalysts consisting of chiral Rh/Ag nanoparticles and Sc(OTf)3have been developed that catalyze asymmetric 1,4-addition reactions of arylboronic acids with α,β-unsaturated amides efficiently. The reaction has been considered one of the most challenging reactions because of the low reactivity of the amide substrates. The new catalysts provide the desired products with outstanding enantioselectivities (>98 % ee) in the presence of low loadings (<0.5 mol %) of the catalyst.

Original languageEnglish
Pages (from-to)8058-8061
Number of pages4
JournalAngewandte Chemie - International Edition
Volume55
Issue number28
DOIs
Publication statusPublished - 4 Jul 2016
Externally publishedYes

Keywords

  • cooperative effects
  • heterogeneous catalysis
  • Lewis acid
  • nanoparticles
  • Rh catalysis

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