Progress in the asymmetric synthetic methodology based on the use of malimides as synthetic equivalents to substituted 2-pyrrolidinones is summarized. The versatile, regio- and diastereo-selective reductive alkylation method developed in these laboratories allows the easy access to trans-5-alkyl-4-benzyloxy-2-pyrrolidinones, which could be further transformed into trans-2-alkyl-3-hydroxypyrroliines or anti-Υ -alkyl-Υ-amino-β-hydroxy acids. The studies along this array thus open an avenue to the asymmetric synthesis of nemonapride, anisomycin, pyrrolam A, the Υ-amino-β-hydroxy acid residue of hapalosin as well as an activated form of (3S, 4R)-ACHPA, a statine analogue.

Key words: IMIDE, ALKYLATION, PYRROLIDINE P, PYRROLIDONE P, MALIC ACID P