The Journal of organic chemistry

The cycloaddition of nitrones with homochiral cyclopropanes

K Sapeta, MA Kerr

Index: Young, Ian S.; Kerr, Michael A. Journal of the American Chemical Society, 2007 , vol. 129, # 5 p. 1465 - 1469

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Citation Number: 87

Abstract

The cycloaddition of nitrones and enantiomerically pure cyclopropane-1, 1-dicarboxylates is examined. Transfer of optical activity to the adduct is dictated by thermal reaction conditions and nature of cyclopropane substitution. Optically active 2-substituted cyclopropane-1, 1- dicarboxylates are shown to racemize under typical reaction conditions, providing evidence for a zwitterionic ring-opened intermediate.