The use of trifluoroacetaldehyde ethyl hemiacetal or hydrate in a simple and practical regioselective synthesis of β-hydroxy-β-trifluoromethyl ketones from enamines and imines

被引：43

作者：

Funabiki, K ^{[1
]}

Matsunaga, K ^{[1
]}

Nojiri, M ^{[1
]}

Hashimoto, W ^{[1
]}

Yamamoto, H ^{[1
]}

Shibata, K ^{[1
]}

Matsui, M ^{[1
]}

机构：

[1] Gifu Univ, Fac Engn, Dept Mat Sci & Technol, Gifu 5011193, Japan

来源：

JOURNAL OF ORGANIC CHEMISTRY | 2003年 / 68卷 / 07期

关键词：

D O I：

10.1021/jo026697j

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The reaction of trifluoroacetaldehyde ethyl hemiacetal or hydrate with an equimolar amount of enamines, derived from various methyl ketones, smoothly proceeded to give the corresponding beta-hydroxy-beta-trifluoromethyl ketones in high yields. An equimolar amount of imines derived from various methyl ketones with aliphatic, aromatic, and heteroaromatic substituents also readily reacted with trifluoroacetaldehyde ethyl hemiacetal or hydrate to afford the corresponding beta-hydroxy-beta-trifluoromethyl ketones in good to excellent yields. Difluoroacetaldehyde ethyl hemiacetal as well as pentafluoropropionaldehyde also participated in the reaction, affording good yields of the corresponding beta-hydroxy-beta-difluoromethyl or beta-pentafluoropropyl ketones.

引用

页码：2853 / 2860

页数：8

共 93 条

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