TiCl4-n-Bu4NX (X = I, Br, and Cl) combination-induced coupling of α,β-unsaturated ketones with aldehydes

被引：36

作者：

Han, ZF ^{[1
]}

Uehira, S ^{[1
]}

Shinokubo, H ^{[1
]}

Oshima, K ^{[1
]}

机构：

[1] Kyoto Univ, Grad Sch Engn, Dept Chem Mat, Kyoto 6068501, Japan

来源：

JOURNAL OF ORGANIC CHEMISTRY | 2001年 / 66卷 / 23期

关键词：

D O I：

10.1021/jo016054o

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A three-component coupling reaction between vinyl ketones, aldehydes, and halides has been developed with TiCl4-n-Bu4NX combined reagents. Treatment of vinyl ketones with a TiCl4-n-Bu4NI combination followed by an addition of a variety of aldehydes provides syn-alpha -iodomethyl-beta -hydroxy ketones with high stereoselectivity. Methyltriphenylphosphonium iodide as well as n-Bu4NI acts efficiently as a halide source. The combination of TiCl4-n-Bu4NBr provides the corresponding bromo compounds in good yields. syn-alpha -Chloromethyl-beta -hydroxy ketones are obtained with the TiCl4-n-Bu4NCl combination. A competitive experiment reveals that the order of relative reactivity of the combinations is TiCl4-n-Bu4NI > TiCl4-n-Bu4NBr > TiCl4-n-Bu4NCl.

引用

页码：7854 / 7857

页数：4

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