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
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
收藏
页码:3510 / 3515
页数:6
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