Successive treatment of a phenyl thioether derived from (S)-malic acid with n-BuLi, lithium naphthalenide (LN), and electrophiles led to 4-hydroxy-3-substituted 2-pyrrolidinones in one- pot and in high regio-and diastereoselectivity at C-3. N-Debenzylation of 1-benzyl-4-hydroxy- 2-pyrrolidinone using LN afforded naturally occurring (−)-(S)-4-hydroxy-2-pyrrolidinone.(−)- (3S, 4S)-4-Hydroxy-3-methyl-2-pyrrolidinone, the lactam form of the γ-amino acid residue ...
