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

被引：82

作者：

Huang, PQ ^{[1
]}

Wang, SL ^{[1
]}

Ye, JL ^{[1
]}

Ruan, YP ^{[1
]}

Huang, YQ ^{[1
]}

Zheng, H ^{[1
]}

Gao, JX ^{[1
]}

机构：

[1] Xiamen Univ, Dept Chem, Xiamen 361005, Fujian, Peoples R China

来源：

TETRAHEDRON | 1998年 / 54卷 / 41期

关键词：

D O I：

10.1016/S0040-4020(98)00734-0

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

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, emonapride, and the unnatural enantiomer of the beta-hydroxy-gamma-amino acid residue of hapalosin in lactam form. (C) 1998 Elsevier Science Ltd. All rights reserved.

引用

页码：12547 / 12560

页数：14

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