Diels-Alder reactions of [(S)R]-(1E,3E)-1-p-tolylsulfinyl-1,3-pentadiene: The unexpected evolution of maleic anhydride adducts.

被引：26
作者：
Carreno, MC
Cid, MB
Ruano, JLG
机构：
[1] Depto. de Quimica Organica (C-I), Universidad Autónoma, Cantoblanco
来源：
TETRAHEDRON-ASYMMETRY | 1996年 / 7卷 / 07期
关键词：
D O I：
10.1016/0957-4166(96)00258-3
中图分类号：
O61 [无机化学];
学科分类号：
070301 ; 081704 ;
摘要：
The Diels-Alder adducts resulting in the reaction of enantiomerically pure [(S)R]-(1E,3E)-1-p-tolylsulfinyl-1,3-pentadiene with maleic anhydride evolved stereoselectively in situ through several intramolecular tandem reactions, involving [2,3]-sigmatropic sulfoxide-sulfenate rearrangement, acylation of the sulfinyl oxygen, and elimination of the sulfur function through a S(N)2' process yielding lactones 3 and 4. Copyright (C) 1996 Elsevier Science Ltd
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页码：2151 / 2158
页数：8
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