Synthesis 2007(14): 2107-2114  
DOI: 10.1055/s-2007-983725
PAPER
© Georg Thieme Verlag Stuttgart · New York

Gold(I)-Catalyzed Rearrangement of Propargylic Alcohols to α,β-Unsaturated Ketones

Sang Ick Lee, Ji Young Baek, So Hee Sim, Young Keun Chung*
Intelligent Textile System Research Center and Department of Chemistry, College of Natural Sciences, Seoul National University, Seoul 151-747, Korea
Fax: +82(2)8890310; e-Mail: ykchung@snu.ac.kr;
Further Information

Publication History

Received 14 March 2007
Publication Date:
03 July 2007 (online)

Abstract

We have developed a gold(I)-catalyzed rearrangement of propargylic alcohols to α,β-unsaturated ketones. The reaction might proceed through a dehydration of an alkynol, followed by an addition of water to a cumulene intermediate. The substituents of the alkynol play an important role in the rearrangement.