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

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.