Lewis acid mediated nucleophilic ring opening followed by cycloaddition of 2-aryl-N-tosylaziridines with carbonyl compounds:: further support towards an SN2-type mechanism

被引：58
|
作者：
Ghorai, Manas K. [1 ]
Ghosh, Koena [1 ]
机构：
[1] Indian Inst Technol, Dept Chem, Kanpur 208016, Uttar Pradesh, India
来源：
TETRAHEDRON LETTERS | 2007年 / 48卷 / 18期
关键词：
2-aryl-N-tosylaziridine; Cn(OTf)(2); Zn(OTf)(2); BF3 center dot OEt2; nucleophilic ring opening; S(N)2 pathway; mechanism; carbonyl; 1,3-oxazolidine; 1,2-amino alcohol;
D O I：
10.1016/j.tetlet.2007.03.042
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
A highly regioselective S(N)2-type ring opening of 2-aryl-N-tosylaziridines with carbonyl compounds in the presence of a Lewis acid to afford various 1,3-oxazolidines and 1,2-amino alcohols in excellent yields and moderate to high enantioselectivity is described. The formation of non-racemic products provides convincing evidence for the S(N)2-type ring opening mechanism. (c) 2007 Elsevier Ltd. All rights reserved.
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收藏
页码：3191 / 3195
页数：5
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