Enantioselective Synthesis of α-Tertiary Hydroxyaldehydes by Palladium-Catalyzed Asymmetric Allylic Alkylation of Enolates

Barry M. Trost,* Jiayi Xu, and Markus Reichle
Department of Chemistry, Stanford University, Stanford, California 94305-5080
J. Am. Chem. Soc., 2007, 129 (2), pp 282–283
DOI: 10.1021/ja067342a
Publication Date (Web): December 20, 2006
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.

, bmtrost@stanford.edu

Abstract

Abstract Image

Chiral α-tertiary hydroxyaldehydes are very versatile building blocks in synthetic chemistry. Herein, we report the first examples of a catalytic asymmetric protocol for the synthesis of such compounds from readily available α-halo or α-hydroxy ketones or enol silyl ethers with excellent yields and enantioselectivity. Its synthetic utility is demonstrated in the short, efficient formal synthesis of (S)-oxybutynin. In this process, the chiral ligand controls the regioselectivity as well as the enantioselectivity.

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History

  • Published In Issue January 17, 2007
  • Received October 12, 2006

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