New chiral sulfoxide ligands in catalytic asymmetric Diels-Alder reactions: double acceleration by the chiralities of the sulfoxides and oxazolines

被引：40

作者：

Hiroi, K ^{[1
]}

Watanabe, K ^{[1
]}

Abe, I ^{[1
]}

Koseki, M ^{[1
]}

机构：

[1] Tohoku Pharmaceut Univ, Aoba Ku, Sendai, Miyagi 9818558, Japan

来源：

TETRAHEDRON LETTERS | 2001年 / 42卷 / 43期

关键词：

D O I：

10.1016/S0040-4039(01)01646-X

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

New chiral sulfoxide ligands which are useful for catalytic asymmetric Diels-Alder reactions have been developed. The new ligands involve a chiral sulfinyl function and a 1,3-oxazoline ring with an asymmetric carbon center, in which the chiral sulfinyl group has been revealed to play a crucial role in achieving high enantioselectivity in asymmetric Diels-Alder reactions. Among the Lewis acid catalysts employed, magnesium iodide provided the highest chemical and stereochemical efficiency in the cycloaddition reactions. A mechanistic pathway for the asymmetric synthesis is proposed on the basis of the stereochemical outcomes obtained. (C) 2001 Elsevier Science Ltd. All rights reserved.

引用

页码：7617 / 7619

页数：3

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