Titanium isopropoxide as efficient catalyst for the aza-Baylis-Hillman reaction.: Selective formation of α-methylene-β-amino acid derivatives
Titanium isopropoxide as efficient catalyst for the aza-Baylis-Hillman reaction.: Selective formation of α-methylene-β-amino acid derivatives
复制标题
DOI：
10.1021/jo0163952
复制
发表时间：
2002-04-05
影响因子：
3.6
通讯作者：
Adolfsson, H
中科院分区：
文献类型：
--
作者：
Balan, D;Adolfsson, H
α-亚甲基-β-氨基酸衍生物的直接形成使用Baylis-Hillman方案的氮杂版本实现。该产物容易在芳基醛、磺酰胺和α，β-不饱和羰基化合物之间的三组分一锅反应中形成。在分子筛存在下，异丙醇钛和2-羟基奎宁环有效地催化了该反应。该协议允许结构变化的基板，容忍电子贫和富电子的芳基醛和各种迈克尔受体。
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.