Stereocontrolled Access to all-transα,β,γ-Substituted Pyrrolidinones and Pyrrolidines of High Optical Purity from D-Pyroglutamic Acid

Authors:
  • SHStephen Hanessian
    Stephen Hanessian
  • VRVirginie Ratovelomanana
    Virginie Ratovelomanana
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Abstract
A procedure was developed for the stereocontrolled conjugate addition of dialkyllithiocuprates to an α,β-unsaturated lactam (3-phenyl-1H,3H-pyrrolo[1,2-c] oxazol-5(7a)-one) derived from D-pyroglutamic acid (D-2-pyrrolidone-5-carboxylic acid). Formation of the corresponding enolates and treatment with alkyl halides, aldehydes or acetone gave α,β,γ-substituted pyrrolidinones and pyrrolidines of high optical purity.