The Problem

N-Substituted pyrrolidin-3-ones (1) undergo enolisation to give the C(4) enolate (3) preferentially.1

beta-Keto ester dianion as a C(2) enolate equivalent.2

C(2)-enolates of pyrrolidin-3-ones have been generated from a beta-ketoester dianion (4) and this strategy has been applied in the synthesis of polyhydroxy indolizidines (6).2

Aims

  • Study the enolisation of the pyrrolidin-3-one system

  • Direct enolisation towards C(2)

  • C-C bond forming reactions on the C(2) enolate using Mukaiyama aldol conditions,3 fluoride ion-mediated4 and TMSOTF-catalysed aldol-type reactions.5

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    Summary