The Diels-Alder cycloaddition reaction of some substituted furans and E-1,2-bis(phenylsulfonyl)ethylene

被引：16

作者：

Arjona, O ^{[1
]}

Iradier, F

Mañas, RM

Plumet, J

Grabuleda, X

Jaime, C

机构：

[1] Univ Complutense Madrid, Fac Quim, Dept Quim Organ 1, E-28040 Madrid, Spain

[2] Univ Autonoma Barcelona, Dept Quim, E-08193 Barcelona, Spain

来源：

TETRAHEDRON | 1998年 / 54卷 / 31期

关键词：

D O I：

10.1016/S0040-4020(98)00547-X

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The Diels-Alder cycloaddition between several 2-, and 3-substituted furans and E-1,2-bis(phenylsulfonyl)ethylene have been carried out in high yields. Stereoselectivity observed in the case of 2-sustituted furans has been explained by means of the MM3-transition state model. The model had to be refined for 2-methoxyfuran due to the asymmetry induced over the transition state geometry by the electron-donating methoxyl group. Selectivity in 2-substituted furans arose by interactions between the 2-substituent and the sulfonyl groups (steric repulsion with the cis-sulfonyl or long-range favourable interactions with the trans-sulfonyl). (C) 1998 Elsevier Science Ltd. All rights reserved.

引用

页码：9095 / 9110

页数：16

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