Stereoselective Enol Tosylation:  Preparation of Trisubstituted α,β-Unsaturated Esters

Jenny M. Baxter,* Dietrich Steinhuebel,* Michael Palucki, and Ian W. Davies;
Department of Process Research, Merck & Co., Inc., P.O. Box 2000, Rahway, New Jersey 07065
Org. Lett., 2005, 7 (2), pp 215–218
DOI: 10.1021/ol047854z
Publication Date (Web): December 17, 2004
Copyright © 2005 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.

, jenny_baxter@merck.com, ; , dietrich_steinhuebel@merck.com

Abstract

Abstract Image

The stereoselective preparation of (E)- or (Z)-trisubstituted α,β-unsaturated esters in three steps from N-protected glycine is presented. The key step in the synthesis is the highly selective enol tosylation of γ-amino β-keto esters. The enol tosylates are stable, crystalline compounds that undergo smooth and effective Suzuki−Miyaura coupling reaction with a variety of aryl boronic acids.

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History

  • Published In Issue January 20, 2005
  • Received October 18, 2004

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