A new approach to (S)-4-hydroxy-2-pyrrolidinone and its 3-substituted analogues

被引：47

作者：

Huang, PQ ^{[1
]}

Zheng, XA ^{[1
]}

Wang, SL ^{[1
]}

Ye, JL ^{[1
]}

Jin, LR ^{[1
]}

Chen, Z ^{[1
]}

机构：

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

来源：

TETRAHEDRON-ASYMMETRY | 1999年 / 10卷 / 17期

关键词：

D O I：

10.1016/S0957-4166(99)00321-3

中图分类号：

O61 [无机化学];

学科分类号：

070301 ; 081704 ;

摘要：

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 y-amino acid residue found in marine natural products, bistramides, was prepared by the same method. (C) 1999 Elsevier Science Ltd. All rights reserved.

引用

页码：3309 / 3317

页数：9

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