β-Ketoester dianions as regiospecific enolate equivalents for N-substituted pyrrolidin-3-ones

M Giles, MS Hadley, T Gallagher

Index: Giles, Melvyn; Hadley, Michael S.; Gallagher, Timothy Journal of the Chemical Society, Chemical Communications, 1990 , # 15 p. 1047 - 1048

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Citation Number: 10

Abstract

Double deprotonation of P-ketoester (6) gives dianion (7) which serves as a synthetic equivalent of the regiospecific ketone enolate (3), providing a synthetic entry to 2-substituted pyrrolidin-3-ones (9) and (10). ... The synthetic utility of enolates derived from heterocyclic ketones such as pyrrolidin-3-ones is limited by the level of regiocontrol that can be exercised in the enolization step. In a comprehensive study, Garst and co-workers showed that the preferred mode of ...