Tetrahedron

Efficient asymmetric synthesis of cis-2-methylcyclopropanecarboxylic acid

T Onoda, R Shirai, N Kawai, S Iwasaki

Index: Onoda, Toshihiko; Shirai, Ryuichi; Kawai, Nobuyuki; Iwasaki, Shigeo Tetrahedron, 1996 , vol. 52, # 42 p. 13327 - 13338

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Citation Number: 16

Abstract

We have developed a versatile method for the synthesis of enantiomerically pure cis-2- methylcyclopropanecarboxylic acid (−)-2, a component of curacin A, and its enantiomer,(+)- 2. Double-asymmetric Simmons-Smith cyclopropanation of the dienes 5 and 9 derived from diethyl L-tartrate proceeded with excellent diastereofacial selectivity (> 99% de) to give the dicyclopropanes 6 and 10, which were converted to both enantiomers of 2.

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