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
收藏
页码：7617 / 7619
页数：3
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