Tetrahedron

A method for the synthesis of cyclopropanes by regiospecific and regioselective magnesium carbenoid 1, 3-CH insertion as the key reactions

H Watanabe, S Ogata, T Satoh

Index: Watanabe, Hiroyuki; Ogata, Shingo; Satoh, Tsuyoshi Tetrahedron, 2010 , vol. 66, # 30 p. 5675 - 5686

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Citation Number: 10

Abstract

Addition reaction of two geometrical isomers of 1-chlorovinyl p-tolyl sulfoxides, derived from unsymmetrical ketones and chloromethyl p-tolyl sulfoxide, with lithium enolate of tert-butyl acetate gave single diastereomers of the adduct, respectively. Treatment of each diastereomer with i-PrMgCl resulted in the formation of magnesium carbenoid. Highly regiospecific 1, 3-CH insertion reaction was found to take place from each magnesium ...