Gold(I)-Catalyzed Isomerization of Allenyl Carbinol Esters:  An Efficient Access to Functionalized 1,3-Butadien-2-ol Esters

Andrea K. Buzas, Florin M. Istrate, and Fabien Gagosz*
Laboratoire de Synthse Organique, UMR 7652 CNRS/Ecole Polytechnique, Ecole Polytechnique, 91128 Palaiseau, France
Org. Lett., 2007, 9 (6), pp 985–988
DOI: 10.1021/ol063031t
Publication Date (Web): February 13, 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.

, gagosz@dcso.polytechnique.fr

Abstract

Abstract Image

A study concerning the gold(I)-catalyzed rearrangement of diversely substituted allenyl carbinol esters into functionalized 1,3-butadien-2-ol esters is described. The mild conditions employed allow the efficient, rapid, and stereoselective synthesis of a variety of such compounds via a new 1,3-shift of an ester moiety onto a gold-activated allene.

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History

  • Published In Issue March 15, 2007
  • Received December 15, 2006

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