Dimethyl sulfide-boron trihalide-mediated reactions of α,β-unsaturated ketones with aldehydes:: one-pot synthesis of Baylis-Hilman adducts and α-halomethyl enones

被引：23

作者：

Iwamura, T ^{[1
]}

Fujita, M ^{[1
]}

Kawakita, T ^{[1
]}

Kinoshita, S ^{[1
]}

Watanabe, S ^{[1
]}

Kataoka, T ^{[1
]}

机构：

[1] Gifu Pharmaceut Univ, Gifu 5028585, Japan

来源：

TETRAHEDRON | 2001年 / 57卷 / 40期

关键词：

aldols; aldol reactions; Baylis-Hillman reactions; boron and compounds; dehydration; Micheal reactions;

D O I：

10.1016/S0040-4020(01)00842-0

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The reactions of aldehydes with 3-buten-2-one (2) were conducted in the presence of (BBr3Me2S)-Me-. or BCl3-Me2S and then worked up with aqueous NaHCO3, affording the a-methylene aldol 3, (alpha -halomethyl aldol 4 or 6, and a-halomethyl enones 5 or 7, respectively. In contrast, the reactions quenched with water gave the alpha -halomethyl enones 5 or 7 in high yields, while the work-up with an aqueous 10% trimethylamine gave the alpha -methylene aldol 3. The phenol 15 and half-acetal 16 were obtained from the reaction of p-nitrobenzaldehyde (1a) with cyclohexenone (10). (C) 2001 Elsevier Science Ltd. All rights reserved.

引用

页码：8455 / 8462

页数：8

共 38 条

[1] Synthetic applications of the Baylis-Hillman adducts:: A simple stereoselective synthesis of (E)-3-(nitroxymethyl)alk-3-en-2-ones [J].