Stereochemical study of a Lewis acid-promoted reaction of 2-silyloxypyrrole with aliphatic and aromatic aldehydes

被引：15

作者：

Uno, H

Nishihara, Y

Mizobe, N

Ono, N

机构：

[1] Ehime Univ, Adv Instrumentat Ctr Chem Anal, Matsuyama, Ehime 7908577, Japan

[2] Ehime Univ, Fac Sci, Dept Chem, Matsuyama, Ehime 7908577, Japan

来源：

BULLETIN OF THE CHEMICAL SOCIETY OF JAPAN | 1999年 / 72卷 / 07期

关键词：

D O I：

10.1246/bcsj.72.1533

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

In the presence of BF3 OEt2, the reaction of 1-t-butoxycarbonyl-2-t-butyldimethylsiloxypyrrole with aliphatic and aromatic aldehydes in ether occurred stereoselectively to give the corresponding erythro and threo isomers, respectively, while a similar reaction in the presence of SnCl4 showed completely opposite selectivity. The transition states leading to the major isomers are discussed.

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页码：1533 / 1539

页数：7

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