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
收藏
页码：2951 / 2953
页数：3
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