Efficient and Stereoselective
Rearrangement of Baylis-Hillman Acetates Catalyzed
by Gold(I) Chloride/Silver(I) Trifluoromethanesulfonate

Yunkui Liu; Dajie Mao; Jianqiang Qian; Shaojie Lou; Zhenyuan Xu; Yongmin Zhang

doi:10.1055/s-0028-1087971

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Synthesis 2009(7): 1170-1174
DOI: 10.1055/s-0028-1087971

PAPER

Efficient and Stereoselective Rearrangement of Baylis-Hillman Acetates Catalyzed by Gold(I) Chloride/Silver(I) Trifluoromethanesulfonate

Yunkui Liu^a, Dajie Mao^a, Jianqiang Qian^a, Shaojie Lou^a, Zhenyuan Xu*^a, Yongmin Zhang^b
^a State Key Laboratory Breeding Base of Green Chemistry-Synthesis Technology, Zhejiang University of Technology, 310014 Hangzhou, P. R. of China
Fax: +86(571)88320609; e-Mail: greensyn@zjut.edu.cn;
^b Department of Chemistry, Zhejiang University, Xi-xi Campus, 310028 Hangzhou, P. R. of China

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Publication History

Received 24 October 2008
Publication Date:
24 February 2009 (online)

Abstract
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Abstract

Efficient and stereoselective rearrangement catalyzed by only one mole-percent gold(I) chloride/silver(I) trifluoromethanesulfonate of Baylis-Hillman acetates afforded 2-(acetoxymethyl)alk-2-enoates under mild reaction conditions in good to high yields with 100% E-selectivity. For cyclohex-2-enone-derived Baylis-Hillman acetates, the reaction gave 2-alkylidenecyclohex-3-enones in good yields.

Key words

gold/silver catalysis - stereoselectivity - rearrangements - Baylis-Hillman acetate - alk-2-enoates

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A referee commented that the loss of 1,3-diaxial repulsion between the methoxycarbonyl or R group and the acetal oxygens may be another factor why intermediate 7 is not destabilized so much (see Scheme [5] ).