One-Pot Method for Stereoselective Cyclopropanation of Electron-Deficient Olefins with Methyl Bromoacetate and Phenacyl Bromide in the Presence of Triphenylarsine

Zhongjiao Ren; Weiguo Cao; Weiyu Ding; Yu Wang

doi:10.1055/s-2005-916035

PAPER

One-Pot Method for Stereoselective Cyclopropanation of Electron-Deficient Olefins with Methyl Bromoacetate and Phenacyl Bromide in the Presence of Triphenylarsine

Zhongjiao Ren*^a, Weiguo Cao^a,b, Weiyu Ding^a, Yu Wang^a
^a Department of Chemistry, Shanghai University, Shanghai, 200444, P. R. of China
Fax: +86(21)66134856; e-Mail: renrui198229@hotmail.com;
^b State Key Laboratory of Organometallic Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, Shanghai, 200032, P. R. of China

Abstract

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Abstract

A triphenylarsine-catalyzed one-pot procedure for the preparation of cis-cyclopropanes with acyclic electron-deficient olefins with carbonyl-stabilized arsonium ylides formed from methyl bromoacetate or phenacyl bromide in the presence of NaHCO₃ has been achieved. This method is simple, high-yielding and cis-selective. The success of this method depends on the choice of base, solvent and temperature.

Key words

one-pot - triphenylarsine - cyclopropanation - stereoselectivity - NaHCO₃

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Referenzen

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