The first enantioselective synthesis of both Diels-Alder enantiomers with the same bis(oxazoline)-magnesium perchlorate chiral catalyst.

被引：71

作者：

Desimoni, G

Faita, G

Righetti, PP

机构：

[1] Dipto. di Chim. Organ. Dell'Univ., Università di Pavia, I-27100 Pavia

来源：

TETRAHEDRON LETTERS | 1996年 / 37卷 / 17期

关键词：

D O I：

10.1016/0040-4039(96)00460-1

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The Diels-Alder reaction between cyclopentadiene and 3-acryloyl-1,3-oxazolin-2-one has been found to occur enantioselectively in the presence of catalytic amounts of (R)-2,2'-isopropylidene-bis(4-phenyl-2-oxazoline) and magnesium perchlorate. From a tetrahedral coordination of catalyst and dienophile the (S)-enantiomer is obtained. if two equivalents of water are added, the coordination occurs with an octahedral geometry and the same catalyst gives the (R)-enantiomer selectively. (C) 1996 Elsevier Science Ltd

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页码：3027 / 3030

页数：4

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