Stereoselective Preparation of (Z)-γ-Silyl-γ,δ-Unsaturated Ketones and their Application in the Synthesis of 1,4-Diketones

Weixin  Zheng; Xian  Huang

doi:10.1055/s-2002-35624

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Synthesis 2002(17): 2497-2502
DOI: 10.1055/s-2002-35624

PAPER

Stereoselective Preparation of (Z)-γ-Silyl-γ,δ-Unsaturated Ketones and their Application in the Synthesis of 1,4-Diketones

Weixin Zheng^a, Xian Huang*^a,b
^a Department of Chemistry, Zhejiang University (Xixi Campus, Hangzhou 310028, P. R. China
^b The State Key Laboratory of Organometallic Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, P. R. China
e-Mail: huangx@mail.hz.zj.cn;

Further Information

Publication History

Received 12 July 2002
Publication Date:
20 November 2002 (online)

Abstract
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Abstract

Hydrozirconation reaction of alkynylsilanes 1 followed by Michael addition to α,β-unsaturated ketones in the presence of CuBr·Me₂S complex produced (Z)-γ-silyl-γ,δ-unsaturated ketones 3 stereoselectively. 1,4-Diketones were prepared via epoxidation and hydrolysis of 3.

Key words

silicon - zirconium - Michael additions - ketones - enones - alkynes

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CCDC-189354 contains the supplementary crystallographic data for this paper.