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-hydroxypyrrolidines or anti-gamma-alkyl-gamma-amino-beta-hydroxy acids. The studies along this array thus open an avenue to the asymmetric synthesis of nemonapride, anisomycin, pyrrolam A, the gamma-amino-beta-hydroxy acid residue of hapalosin as well as an activated form of (3s, 4R)-ACHPA, a statine analogue.