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.

引用

页码：3191 / 3195

页数：5

共 3 条

[1] Lewis acid mediated SN2-type nucleophilic ring opening followed by [4+2] cycloaddition of N-tosylazetidines with aldehydes and ketones:: synthesis of chiral 1,3-oxazinanes and 1,3-amino alcohols
Ghorai, Manas K.
Das, Kalpataru
Kumar, Amit
TETRAHEDRON LETTERS, 2007, 48 (25) : 4373 - 4377
[2] SN2-type ring opening of substituted-N-tosylaziridines with zinc (II) halides: Control of racemization by quaternary ammonium salt
Ghorai, Manas K.
Tiwari, Deo Prakash
Kumar, Amit
Das, Kalpataru
JOURNAL OF CHEMICAL SCIENCES, 2011, 123 (06) : 951 - 961
[3] SN2-type ring opening of substituted-N-tosylaziridines with zinc (II) halides: Control of racemization by quaternary ammonium salt
Ghorai M.K.
Tiwari D.P.
Kumar A.
Das K.
Journal of Chemical Sciences, 2011, 123 (6) : 951 - 961

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