Lewis base catalyzed enantioselective additions of an N-silyl vinylketene imine

Scott E. Denmark, Tyler W. Wilson

Research output: Contribution to journalArticle

Abstract

Outside the limits: In the title reaction the nucleophile 1 represents a synthetic equivalent of nucleophilic allylic nitriles and addresses some of the current limitations associated with reactions of allylic nitrile anions. Unsaturated nitriles containing a trisubstituted double bond are obtained in high yield, with excellent site selectivity and good to excellent stereoselectivity (see scheme; LDA=lithium diisopropylamide).

Original languageEnglish (US)
Pages (from-to)3236-3239
Number of pages4
JournalAngewandte Chemie - International Edition
Volume51
Issue number13
DOIs
StatePublished - Mar 26 2012

Keywords

  • Lewis bases
  • allylic compounds
  • asymmetric catalysis
  • enantioselectivity
  • ketenes

ASJC Scopus subject areas

  • Catalysis
  • Chemistry(all)

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