N-Heterocyclic Carbene-Initiated α-Acylvinyl Anion Reactivity:  Additions of α-Hydroxypropargylsilanes to Aldehydes

Troy E. Reynolds, Charlotte A. Stern, and Karl A. Scheidt*
Department of Chemistry, Northwestern University, Evanston, Illinois 60208
Org. Lett., 2007, 9 (13), pp 2581–2584
DOI: 10.1021/ol0710515
Publication Date (Web): June 1, 2007
Copyright © 2007 American Chemical Society
*

In papers with more than one author, the asterisk indicates the name of the author to whom inquiries about the paper should be addressed.

, scheidt@northwestern.edu

Abstract

Abstract Image

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.

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History

  • Published In Issue June 21, 2007
  • Received May 5, 2007

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