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

被引：39

作者：

Ghorai, Manas K. ^{[1
]}

Das, Kalpataru ^{[1
]}

Kumar, Amit ^{[1
]}

机构：

[1] Indian Inst Technol, Dept Chem, Kanpur 208016, Uttar Pradesh, India

来源：

TETRAHEDRON LETTERS | 2007年 / 48卷 / 25期

关键词：

N-tosylazetidine; nucleophilic; ring opening; carbonyl; Lewis acid; Cu(OTT)(2); 4+2] cycloaddition; 1,3-oxazinane; 1,3-amino alcohol; non-racemic; S(N)2; mechanism;

D O I：

10.1016/j.tetlet.2007.04.097

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A highly efficient strategy for Cu(OTf)(2) mediated S(N)2-type nucleophilic ring opening followed by [4+2] cycloaddition reactions of enantiopure 2-phenyl-N-tosylazetidines with various aldehydes and ketones afforded a variety of substituted 1,3-oxazinanes and 1,3-amino alcohols in excellent yields, excellent de and good to excellent ee. The proposed S(N)2-type mechanism of the cycloaddition reaction is supported by experimental evidence. (c) 2007 Elsevier Ltd. All rights reserved.

引用

页码：4373 / 4377

页数：5

共 15 条

[1] Lewis acid-mediated highly regioselective SN2-Type ring-opening of 2-Aryl-N-tosylazetidines and aziridines by alcohols
Ghorai, Manas K.
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JOURNAL OF ORGANIC CHEMISTRY, 2007, 72 (15): : 5859 - 5862
[2] An efficient synthetic route to substituted tetrahydropyrimidines by Cu(OTf)O2-mediated nucleophilic ring-opening followed by the [4+2] cycloaddition of N-tosylazetidines with nitriles
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[3] Lewis acid mediated nucleophilic ring opening followed by cycloaddition of 2-aryl-N-tosylaziridines with carbonyl compounds:: further support towards an SN2-type mechanism
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TETRAHEDRON LETTERS, 2007, 48 (18) : 3191 - 3195
[4] Organocatalytic Enantioselective Synthesis of 1,3-Oxazinanes and Hexahydropyrimidines via [4+2]-Annulation of Cyclic N-Sulfimines
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[6] N-thioacyl 1,3-amino alcohols:: Synthesis via ring-opening of oxiranes with thioamide dianions and applications as key intermediates leading to stereochemically defined 5,6-dihydro-4H-1,3-oxazines and 1,3-amino alcohols
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[7] 1ST [4+2] CYCLOADDITION REACTION BETWEEN VINYL FISCHER TYPE CARBENE COMPLEXES AND CHIRAL 2-AMINO-1,3-DIENES
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[8] Base-catalyzed [3+2]/[4+2]-annulations of cyclic N-sulfimines with γ- and δ-sulfonamido/hydroxy-α,β-unsaturated carbonyls: Stereoselective synthesis of imidazolidines, oxazolidines, hexahydropyrimidines, and 1,3-oxazinanes
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[9] Umpolung of chiral 2-ethynylaziridines: Indium(I)-mediated stereoselective synthesis of nonracemic 1,3-amino alcohols bearing three chiral centers, catalyzed by palladium(0)
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[10] Regioselective [4+2] cycloaddition versus nucleophilic reactions of N-arylamino substituted 1,3-diaza-1,3-butadienes with ketenes: Synthesis of pyrimidinone and fused pyrimidinone derivatives .2.
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