Enantioselective Diels-Alder reactions with N-hydroxy-N-phenylacrylamide

被引：38

作者：

Corminboeuf, O ^{[1
]}

Renaud, P ^{[1
]}

机构：

[1] Univ Bern, Dept Chem & Biochem, CH-3000 Bern, Switzerland

来源：

ORGANIC LETTERS | 2002年 / 4卷 / 10期

关键词：

D O I：

10.1021/ol025799t

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

[GRAPHICS] The use of hydroxamic acids as templates for Lewis acid catalyzed enantioselective Diels-Alder reactions has been examined. A very simple chiral Lewis acid, prepared by mixing optically pure binaphthol with 3 equiv of trimethylaluminum, catalyzes the [4 + 2] cycloaddition of N-hydroxy-N-phenylacrylamide with cyclopentadiene at 0 degreesC in high yield (>96%) and with a fairly good level of enantioselectivity (91% ee). Facile conversion of the products to the corresponding alcohols or aldehydes makes the hydroxamic acid intermediates particularly useful.

引用

页码：1731 / 1733

页数：3

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