Enolate formation from cyclopropyl ketones via iodide-induced ring opening and its use for stereoselective aldol reaction

被引：64

作者：

Han, Z ^{[1
]}

Uehira, S ^{[1
]}

Tsuritani, T ^{[1
]}

Shinokubo, H ^{[1
]}

Oshima, K ^{[1
]}

机构：

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

来源：

TETRAHEDRON | 2001年 / 57卷 / 06期

关键词：

cyclopropyl ketones; aldol reaction; nucleophiles;

D O I：

10.1016/S0040-4020(00)01094-2

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Treatment of cyclopropyl ketones with TiCl4-n-Bu4NI mixed reagent provides (Z)-titanium enolates which afford syn-alpha -iodethyl-P-hydroxyketones stereoselectively upon subsequent reaction with various aldehydes. The aldol adducts are cyclized into transacyltetrahydrofurans in good yield by active alumina. In contrast, the nse of Et(2)AII in place of TiCl4-n-Bu4NI provides the corresponding anti aldol adducts with high stereoselectivity. These methods can complementarily provide both syn and anti isomers of alpha -iodoethyl-beta -hydroxyketones from cyclopropyl ketones and aldehydes. (C) 2001 Elsevier Science Ltd. All rights reserved.

引用

页码：987 / 995

页数：9

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