On the mechanism and diastereoselectivity of 2,3-dihydrobenzofuran formation from sulfinylbenzoquinones and 2-trimethylsilyloxyfuran

被引：11

作者：

Carreño, MC ^{[1
]}

Ruano, JLG ^{[1
]}

Urbano, A ^{[1
]}

Remor, CZ ^{[1
]}

Arroyo, Y ^{[1
]}

机构：

[1] Univ Autonoma Madrid, Dept Quim Organ C 1, Madrid, Spain

来源：

TETRAHEDRON-ASYMMETRY | 1999年 / 10卷 / 22期

关键词：

D O I：

10.1016/S0957-4166(99)00460-7

中图分类号：

O61 [无机化学];

学科分类号：

070301 ; 081704 ;

摘要：

A mechanistic study of the reactions between 2-trimethyisilyloxyfuran 1 and (SS)-2-(arylsulfinyl)- 1,4-benzoquinones 2a and 2b, giving rise to the diastereoselective formation of [3aS,8bS,SS]-3a,8b-dihydro-7-hydroxy-8-(arylsulfinyl)furo[3,2-b]benzofuran-2(3H)-ones 3a and 3b, is reported. The detection and H-1 NMR characterization of several precursors of 3a and 3b accounts for a Michael-type initial reaction which dictates the final diastereoselection of the process. A significant improvement of the stereoselectivity (up to 96% de) in the formation of the tert-butylsulfinyl substituted derivative 3c was achieved by using 2-(tert-butylsulfinyl)- 1,4-benzoquinone 2c as the starting quinone. (C) 1999 Elsevier Science Ltd. All rights reserved.

引用

页码：4357 / 4367

页数：11

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