Tetrahedron

An easy access to protected (4S, 5R)-5-alkyl-4-hydroxy-2-pyrrolidinones and their use as versatile synthetic intermediates

PQ Huang, SL Wang, JL Ye, YP Ruan, YQ Huang…

Index: Huang, Pei Qiang; Wang, Shi Li; Ye, Jian Liang; Ruan, Yuan Ping; Huang, You Qing; Zheng, Hong; Gao, Jing Xing Tetrahedron, 1998 , vol. 54, # 41 p. 12547 - 12560

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Citation Number: 78

Abstract

A versatile approach to enantiopure (4S, 5R)-5-alkyl-4-hydroxy-2-pyrrolidinones is described. The key steps involve a regioselective Grignard reagent addition to (S)- malimides, and diastereoselective reductive dehydroxylation of the resulting hemi-azaketals. The flexibility of this methodology has been demonstrated by the synthesis of (2R, 3R)-3- amino-1-benzyl-2-methylpyrrolidine, the parent diamine of antipsychotic agent, ...