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Synlett 1990; 1990(9): 501-503
DOI: 10.1055/s-1990-21141
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Stereocontrolled Access to all-trans α,β,γ-Substituted Pyrrolidinones and Pyrrolidines of High Optical Purity from D-Pyroglutamic Acid

Stephen Hanessian* , Virginie Ratovelomanana
  • *Department of Chemistry, Université de Montréal, C.P. 6128, Succ. A, Montréal, Québec, H3C 3J7, Canada
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Publication Date:
08 March 2002 (online)

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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.

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