Direct catalytic asymmetric addition of allyl cyanide to ketones

Ryo Yazaki, Naoya Kumagai, Masakatsu Shibasaki

Research output: Contribution to journalArticlepeer-review

67 Citations (Scopus)

Abstract

A direct catalytic asymmetric addition of allyl cyanide to ketones with a bimetallic catalytic system comprising (R,R)-Ph-BPE/[Cu(CH3CN) 4]ClO4/LiOAr is described. Exclusive γ-addition of allyl cyanide was observed, affording optically enriched tertiary alcohols bearing Z-configured α,ß-unsaturated nitriles. The reaction proceeded under proton-transfer conditions, utilizing soft Lewis acid/hard Brønsted base bifunctional catalysis. The applicability of the reaction to aromatic, heteroaromatic, and aliphatic ketones demonstrates its wide substrate generality.

Original languageEnglish
Pages (from-to)3195-3197
Number of pages3
JournalJournal of the American Chemical Society
Volume131
Issue number9
DOIs
Publication statusPublished - 2009 Mar 11
Externally publishedYes

ASJC Scopus subject areas

  • Catalysis
  • Chemistry(all)
  • Biochemistry
  • Colloid and Surface Chemistry

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