Novel use of N-benzoyl-N,O-acetals as N-acylimine equivalents in asymmetric heterocycloaddition:: An extended enantioselective pathway to β-benzamido aldehydes

被引：37

作者：

Gizecki, P ^{[1
]}

Dhal, R ^{[1
]}

Poulard, C ^{[1
]}

Gosselin, P ^{[1
]}

Dujardin, G ^{[1
]}

机构：

[1] Univ Maine, Synth Organ Lab, CNRS, UMR 6011, F-72085 Le Mans 9, France

来源：

JOURNAL OF ORGANIC CHEMISTRY | 2003年 / 68卷 / 11期

关键词：

D O I：

10.1021/jo0203138

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

For the first time, easily available N-(alpha-methoxyalkyl)amides were successfully used as synthetic equivalents of N-acylimines in an asymmetric heterocycloaddition process. The facial-controlled formation of 6-alkoxydihydrooxazines was thus achieved by SnCl4-promoted heterocycloaddition of (R)-O-vinyl pantolactone. By simple acidic hydrolysis of the crude heteroadducts, new beta-aryl- and beta-alkyl-substituted benzamido aldehydes were thus obtained in good overall yields with high enantioselectivities.

引用

页码：4338 / 4344

页数：7

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