Tetrahedron letters

Synthesis of cyclopropanols via cyclopropanation of zinc enolates

S Ito, H Shinokubo, K Oshima

Index: Ito, Saeko; Shinokubo, Hiroshi; Oshima, Koichiro Tetrahedron Letters, 1998 , vol. 39, # 29 p. 5253 - 5256

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Citation Number: 12

Abstract

The reaction of α-iodoketones with diethylzinc afforded zinc enolates which were converted into the corresponding cyclopropanols in good yields upon treatment with CH2I2 and Et2Zn. The use of α-iodoketone having a carbon-carbon double bond as a substrate proved that cyclopropanation of the enolate moiety proceeded chemoselectively. Cyclopropanation of the zinc enolates derived from α, β-unsaturated ketones via 1, 4-addition of organozinc ...