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Regio- And Diastereoselective Synthesis Of 5-trans-substituted And 5,5-disubstituted 2-pyrrolidinones Derived From (S)-malic Acid

C. M. Schuch, R. A. Pilli
Published 2002 · Chemistry

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Abstract 5- trans -Substituted 2-pyrrolidinones 6a , 6c and 6d and 5,5-disubstituted 2-pyrrolidinones 6e – k were regio- and diastereoselectively formed through the addition of organolithium species to imides 1a , b derived from malic acid, followed by addition of triethylsilane, allyltributyltin or TMSCN to the N -acyliminium ions formed in situ from the corresponding 5-hydroxy lactams. A short and diastereoselective synthesis of non-natural amino acid trans- 4-hydroxy- d -proline is reported.
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