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Synthesis 2008(24): 3995-4001  
DOI: 10.1055/s-0028-1083248
PAPER
© Georg Thieme Verlag Stuttgart ˙ New York

Highly Stereoselective Synthesis of trans-1,2-Cyclopropane Derivatives from Semistabilized Arsonium Ylides by Phase-Transfer-Catalysis Reactions

Huihui Wanga, Yali Chen*a, Weiguo Cao*a,b, Han Dinga, Jie Chena, Hongmei Dengc, Min Shaoc
a Department of Chemistry, Shanghai University, Shanghai 200444, P. R. of China
e-Mail: ylchen@staff.shu.edu.cn;
b State Key Laboratory of Organometallic Chemistry, Chinese Academy of Sciences, Shanghai 200032, P. R. of China
c Instrumental Analysis and Research Center, Shanghai University, Shanghai 200444, P. R. of China
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Publication History

Received 30 July 2008
Publication Date:
01 December 2008 (online)

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Abstract

Semistabilized arsonium ylides, generated in situ from the corresponding arsonium salts in the biphasic system of dichloromethane-50% aqueous sodium hydroxide, reacted smoothly with electron-deficient alkenes to afford trans-1,2-cyclopropane derivatives with high stereoselectivity. The synthesis of trans-1,2-cyclopropane derivatives in the presence of sodium hexamethyl­-disilazanide (1.0 M solution in THF) were also studied.

Key words

semistabilized arsonium ylide - cyclopropane derivative - phase-transfer catalysis - stereoselectivity

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7

The crystal structure of 4ab has been deposited at the Cambridge Crystallographic Data Centre with the deposition number CCDC 671899. Unit cell parameters: a = 9.5560 (14) Å, b = 10.0612 (15) Å, c = 10.3985 (16) Å, α = 89.764 (2), β = 67.498 (2), γ = 74.565 (2), space group: P 1.