A novel asymmetric synthesis of 2-azetidinones from achiral precursors

被引：13
|
作者：
Zhou, F
Detty, MR [1 ]
Lachicotte, RJ
机构：
[1] SUNY Buffalo, Dept Med Chem, Buffalo, NY 14260 USA
[2] SUNY Buffalo, Dept Chem, Buffalo, NY 14260 USA
[3] Univ Rochester, Dept Chem, Rochester, NY 14627 USA
来源：
TETRAHEDRON LETTERS | 1999年 / 40卷 / 04期
关键词：
D O I：
10.1016/S0040-4039(98)02473-3
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
Asymmetric synthesis of (3S,4S)-3-phenylsulfonyl-4-phenylazetidin-2-ones in up to 46% ee from achiral amines and 2-phenylsulfonyl-3-phenylpropenoyl chloride was achieved with chiral Lewis-acid catalysis by salen-copper(II) complexes derived from (1R, 2R)-(-)-1,2-diaminocyclohexane. The absolute configuration was assigned by single crystal, X-ray crystallographic analyis of enantiomerically pure (3S,4S)-(-)-3-phenylsulfonyl-4-phenylazetidin-2-one (7). (C) 1999 Elsevier Science Ltd. All rights reserved.
引用
收藏
页码：585 / 588
页数：4
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