Tetrahedron

Synthetic studies towards gelsemine, I The importance of the antiperiplanar effect in the highly regioselective reduction of non-symmetrical cis-hexahydrophthalimides

RJ Vijn, H Hiemstra, JJ Kok, M Knotter, WN Speckamp

Index: Vijn, Robert J.; Hiemstra, Henk; Kok, Joost J.; Knotter, Martin; Speckamp, W. Nico Tetrahedron, 1987 , vol. 43, # 21 p. 5019 - 5030

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Citation Number: 44

Abstract

During studies aimed at the total synthesis of gelsemine an exceptional example of regioselectivity has been discovered. cis-Hexahydrophtnalimides, which are non- symmetrical through the presence of one alkyl group (see Figure 1), are reduced by sodium borohydride into the corresponding hydroxy lactams with very high regioselectivity. The corresponding cis-tetrahydrophthalimides exhibit much lower selectivity. These findings ...