Catalytic conjugate addition of acyl anion equivalents promoted by fluorodesilylation

Scott E Denmark, Lindsey R. Cullen

Research output: Contribution to journalArticle

Abstract

The conjugate addition of acyl anion equivalents derived from 2-silyl-1,3-dithianes to α,β-unsaturated ketones and esters has been achieved using a substoichiometric amount of TBAF. High yields and short reaction times are observed for the addition of aryl-1,3-dithianes to a variety of cyclic and acyclic α,β-unsaturated carbonyl acceptors. Observation of the reactive anion by 13C NMR spectroscopy and extension to an asymmetric variant is also presented.

Original languageEnglish (US)
Pages (from-to)70-73
Number of pages4
JournalOrganic Letters
Volume16
Issue number1
DOIs
StatePublished - Jan 3 2014

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ASJC Scopus subject areas

  • Biochemistry
  • Physical and Theoretical Chemistry
  • Organic Chemistry

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