N-alkoxyacrylamides as substrates for enantioselective Diels-Alder reactions

被引：43

作者：

Corminboeuf, O ^{[1
]}

Renaud, P ^{[1
]}

机构：

[1] Univ Bern, Dept Chem & Biochem, CH-3000 Bern 9, Switzerland

来源：

ORGANIC LETTERS | 2002年 / 4卷 / 10期

关键词：

D O I：

10.1021/ol0257981

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

[GRAPHICS] The use of N-alkoxyacrylamides as substrates for Lewis acid catalyzed Diels-Alder reactions has been examined. Enantioselectivities up to 92% ee have been achieved using very simple chiral Lewis acids prepared from triisobutylaluminum and 2,2-dimethyl-alpha,alpha,alpha',alpha'-tetra-1-naphthalenyl-TADDOL (1-NaphtTADDOL). The use of Yamamoto's Zn-BINOL, easily prepared from Et2Zn and 1,1'-bi-2-naphthol (BINOL), proved to be even more efficient, and enantioselectivities up to 96% ee were achieved.

引用

页码：1735 / 1738

页数：4

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