N-heterocyclic carbene-initiated α-acylvinyl anion reactivity: Additions of α-hydroxypropargylsilanes to aldehydes

Troy E. Reynolds, Charlotte A. Stern, Karl A. Scheidt*

*Corresponding author for this work

Research output: Contribution to journalArticle

41 Scopus citations

Abstract

Highly substituted α,β-unsaturated ketones are prepared by the N-heterocyclic carbene-initiated addition of α-hydroxypropargylsilanes to aldehydes. This strategy serves as a highly efficient alternative to the standard Morita-Baylis-Hillman (MBH) approaches for these types of compounds. In contrast to the MBH reaction, different substitution in the β-position of the product (R1) can be accommodated in moderate to excellent yields with a high degree of control over the resulting alkene.

Original languageEnglish (US)
Pages (from-to)2581-2584
Number of pages4
JournalOrganic Letters
Volume9
Issue number13
DOIs
StatePublished - Jun 21 2007

ASJC Scopus subject areas

  • Biochemistry
  • Physical and Theoretical Chemistry
  • Organic Chemistry

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