Investigation into factors influencing stereoselectivity in the reactions of heterocycles with donor-acceptor-substituted rhodium carbenoids

SJ Hedley, DL Ventura, PM Dominiak…

Index: Hedley, Simon J.; Ventura, Dominic L.; Dominiak, Paulina M.; Nygren, Cara L.; Davies, Huw M. L. Journal of Organic Chemistry, 2006 , vol. 71, # 14 p. 5349 - 5356

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Citation Number: 55

Abstract

Rhodium-catalyzed decomposition of aryldiazoacetates in the presence of pyrroles or furans results in mono-or biscyclopropanation of the heterocycle, but with opposite enantioinduction. In the absence of sterically encumbering groups, the cyclopropanation of furan occurs with initial bond formation at the 2-position. If this pathway is sterically blocked, cyclopropanation can occur with initial bond formation at the 3-position of the furan ring; in ...