The aldol reaction of allenolates with aldehydes in the presence of magnesium diiodide (MgI2) as catalyst

被引：21

作者：

Deng, GH ^{[1
]}

Hu, H

Wei, HX

Paré, PW

机构：

[1] GuangXi Univ Nationalities, Dept Chem, Nanning 530006, Peoples R China

[2] Texas Tech Univ, Dept Chem & Biochem, Lubbock, TX 79409 USA

来源：

HELVETICA CHIMICA ACTA | 2003年 / 86卷 / 10期

关键词：

D O I：

10.1002/hlca.200390294

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

Stereoselective synthesis of (Z)-alpha-(hydroxyalkyl)-beta-iodoacrylates (= (2Z)-2-(hydroxyalkyl)-3-iodoprop-2-enoates) was achieved in a one-pot coupling reaction from methyl prop-2-ynoate, Me3SiI, and an alkanal under mild conditions with MgI2 as catalyst (--> 1-9; see Table and Scheme 1). Baylis-Hillman beta-iodo adducts were generated in excellent yields with high (Z)-selectivity. The conversion of methyl prop-2-ynoate to an active methyl 3-iodo-1-[(trimethylsilyl)oxy]allenolate intermediate in situ followed by carbonyl addition is proposed as the reaction sequence (Schemes 1 and 2).

引用

页码：3510 / 3515

页数：6

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