Tetrahedron p. 5019 - 5030 (1987)
Update date:2022-08-05
Topics:
Vijn, Robert J.
Hiemstra, Henk
Kok, Joost J.
Knotter, Martin
Speckamp, W. Nico
During studies aimed at the total synthesis of gelsemine an exceptional example of regioselectivity has been discovered. cis-Hexahydrophthalimides, which are non-symmetrical through the presence of the 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 are explained on the basis of the conformational preference of the imide molecule and the antiperiplanar effect.
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