Lewis acid-catalyzed conjugate additions of silyloxyallenes: A selective solution to the intermolecular Rauhut-Currier problem

Troy E. Reynolds, Michael S. Binkley, Karl A. Scheidt

Research output: Contribution to journalArticlepeer-review

56 Scopus citations

Abstract

(Chemical Equation Presented) Silyloxyallenes serve as highly useful α-acylvinyl anion equivalents. These latent allenolates undergo conjugate additions to alkylidene malonates in the presence of 10 mol % Sc(OTf) 3. The reaction delivers intermolecular Rauhut-Currier products in excellent yields and regioselectivities for a wide scope of substrates. Notably, the formal cross-coupling of two different α,β-unsaturated carbonyl compounds (a cross Rauhut-Currier reaction) is achieved. Preliminary investigations have demonstrated good levels of enantioselectivity for the addition of a racemic silyloxyallene with a chiral Lewis acid.

Original languageEnglish (US)
Pages (from-to)2449-2452
Number of pages4
JournalOrganic Letters
Volume10
Issue number12
DOIs
StatePublished - 2008

ASJC Scopus subject areas

  • Biochemistry
  • Physical and Theoretical Chemistry
  • Organic Chemistry

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