Diels-Alder reactions of (Rs)-3-[(1S)-isoborneol-10-sulfinyl]-1-methoxybuta-1,3-dienes with electron-deficient carbodienophiles.: The effects of Lewis acid catalysis

被引：26

作者：

Aversa, MC

Barattucci, A

Bonaccorsi, P

Giannetto, P

Panzalorto, M

Rizzo, S

机构：

[1] Univ Messina, Dipartimento Chim Organ & Biol, I-98166 Messina, Italy

[2] Univ Messina, Dipartimento Chim Inorgan Chim Analitica & Chim F, I-98166 Messina, Italy

来源：

TETRAHEDRON-ASYMMETRY | 1998年 / 9卷 / 09期

关键词：

D O I：

10.1016/S0957-4166(98)00138-4

中图分类号：

O61 [无机化学];

学科分类号：

070301 ; 081704 ;

摘要：

Uncatalyzed cycloadditions of (R-s,E)-1 and (R-s,2)-3-[(1S)-isoborneol-10-sulfinyl]-1-methoxybuta-1,3-diene 2 with maleimide and N-phenylmaleimide occurred with complete endo and very high facial diastereoselectivities. The effects of Lewis acid catalysis on these Diels-Alder reactions have been evaluated. LiClO4 catalyzed cycloaddition of 1 with dimethyl maleate gave cyclohexene 13 as the unique product with complete control of endo and pi-facial diastereoselectivities exerted by the sulfinyl group. A significant improvement in diastereoselectivity was also observed in the LiClO4 catalyzed cycloaddition of 1 with dimethyl fumarate. (C) 1998 Elsevier Science Ltd. All rights reserved.

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页码：1577 / 1587

页数：11

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