Tetrahedron

Cyclopropanone equivalents from 3-chloropropionic acid. Use of 1-piperidino-1-trimethylsilyloxycyclopropane in synthetic applications

HH Wasserman, RP Dion, J Fukuyama

Index: Wasserman, Harry H.; Dion, Robert P.; Fukuyama, James Tetrahedron, 1989 , vol. 45, # 10 p. 3203 - 3216

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Citation Number: 14

Abstract

1-Piperidino-1-trimethylsilyloxycyclopropane and the corresponding 1-hydroxy-1- piperidinocyclopropane, conveniently prepared from the piperidide of 3-chloropropionic acid, react as cyclopropanone equivalents with various nucleophiles. Use of these derivatives in the formation of pyrroles, pyrrolines and pyrrolizidines is described. The rearrangement of dicyclopropyl ketimines is explored.