Decarboxylative Aldol Reactions of Allyl β-Keto Esters via Heterobimetallic Catalysis

Sha Lou, John A. Westbrook, and Scott E. Schaus*
Department of Chemistry, Metcalf Center for Science and Engineering, Boston University, 590 Commonwealth Avenue, Boston, Massachusetts 02215
J. Am. Chem. Soc., 2004, 126 (37), pp 11440–11441
DOI: 10.1021/ja045981k
Publication Date (Web): August 25, 2004
Copyright © 2004 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.

, seschaus@bu.edu

Abstract

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Mild and selective heterobimetallic-catalyzed decarboxylative aldol reactions involving allyl β-keto esters have been developed. The reaction is promoted by Pd(0)− and Yb(III)−DIOP complexes at room temperature and involves the in situ formation of a ketone enolate from allyl β-keto esters followed by addition of the enolate to aldehydes. The reaction is a new example of heterobimetallic catalysis in which the optimized reaction conditions require the addition of both metals.

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History

  • Published In Issue September 22, 2004
  • Received July 6, 2004

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