Passerini reactions for the efficient synthesis of 3,3-disubstituted oxetanes

被引：14

作者：

Beasley, Benjamin O. ^{[1
]}

Clarkson, Guy J. ^{[1
]}

Shipman, Michael ^{[1
]}

机构：

[1] Univ Warwick, Dept Chem, Coventry CV4 7AL, W Midlands, England

来源：

TETRAHEDRON LETTERS | 2012年 / 53卷 / 24期

基金：

英国工程与自然科学研究理事会;

关键词：

Isocyanide; Multi-component reaction; Oxetane; Passerini reaction;

D O I：

10.1016/j.tetlet.2012.03.065

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Three-component reactions of oxetan-3-ones with isocyanides and carboxylic acids produce 3,3-disubstituted oxetanes in good yields. Good levels of diastereocontrol (dr = 4:1) can be achieved in these Passerini reactions when the oxetane nucleus possesses a bulky cyclohexyl substituent at C-2. The (2S*,3R*)-stereochemistry of the major diastereomer was confirmed by X-ray crystallography after ester hydrolysis, and a possible mechanism to account for the diastereofacial selectivity is presented. (C) 2012 Elsevier Ltd. All rights reserved.

引用

页码：2951 / 2953

页数：3

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