Titanium isopropoxide as efficient catalyst for the aza-Baylis-Hillman reaction.: Selective formation of α-methylene-β-amino acid derivatives

被引：59
|
作者：
Balan, D [1 ]
Adolfsson, H [1 ]
机构：
[1] Stockholm Univ, Dept Organ Chem, SE-10691 Stockholm, Sweden
来源：
JOURNAL OF ORGANIC CHEMISTRY | 2002年 / 67卷 / 07期
关键词：
D O I：
10.1021/jo0163952
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
The direct formation of alpha-methylene-beta-amino acid derivatives is achieved using the aza version of the Baylis-Hillman protocol. The products are readily formed in a three-component one-pot reaction between arylaldehydes, sulfonamides, and alpha,beta-unsaturated carbonyl compounds. The reaction is efficiently catalyzed by titanium isopropoxide and 2-hydroxyquinuclidine in the presence of molecular sieves. The protocol allows for structural variation of the substrates, tolerating electron-poor and electron-rich arylaldehydes and various Michael acceptors.
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页码：2329 / 2334
页数：6
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