Direct catalytic asymmetric addition of allylic cyanides to ketoimines

Ryo Yazaki, Tatsuya Nitabaru, Naoya Kumagai, Masakatsu Shibasaki

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Abstract

Direct catalytic asymmetric addition of allylic cyanides to N-diphenylphosphinoyl ketoimines with a bimetallic catalytic system comprising Ph-BPE/[Cu(CH3CN)4]ClO4/LiOAr is described. Intermediary α-adducts readily isomerized to afford synthetically useful α,β-unsaturated nitriles bearing an optically active tetrasubstituted carbon. Applicability to aromatic, heteroaromatic, and aliphatic ketoimines exemplifies wide substrate generality. Transformation of the product into densely functionalized material showcases the utility of the present protocol.

Original languageEnglish
Pages (from-to)14477-14479
Number of pages3
JournalJournal of the American Chemical Society
Volume130
Issue number44
DOIs
Publication statusPublished - Nov 5 2008
Externally publishedYes

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All Science Journal Classification (ASJC) codes

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

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