One-pot three-step thioconjugate addition-oxidation-Diels-Alder reactions of ethyl propiolate

被引：6

作者：

Downey, C. Wade ^{[1
]}

Craciun, Smaranda ^{[1
]}

Vivelo, Christina A. ^{[1
]}

Neferu, Ana M. ^{[1
]}

Mueller, Carly J. ^{[1
]}

Corsi, Stephanie ^{[1
]}

机构：

[1] Univ Richmond, Dept Chem, Richmond, VA 23173 USA

来源：

TETRAHEDRON LETTERS | 2012年 / 53卷 / 43期

关键词：

Diels-Alder; Lithium; One-pot; Sulfone; Ynoate; Enoate; Thiol; TMSOTF; DIENOPHILES; ACETALS;

D O I：

10.1016/j.tetlet.2012.08.054

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Ethyl propiolate undergoes one-pot three-step thioconjugate addition-oxidation-Diels-Alder cycloaddition when treated with a variety of thiols in the presence of catalytic base, meta-chloroperbenzoic acid, lithium perchlorate, and cyclopentadiene. The reaction of S-aryl thiols is catalyzed by trialkylamines, and the reaction of aliphatic thiols requires catalytic alkoxide base. Yields of the major diastereomer of the conveniently functionalized bicyclic products range from 47% to 81% depending upon the thiol reactant, which compares favorably to yields observed when the entire synthesis is performed step-by-step. (C) 2012 Elsevier Ltd. All rights reserved.

引用

页码：5766 / 5768

页数：3

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