Asymmetric cross aldol addition of isatins with α,β-unsaturated ketones catalyzed by a bifunctional Bronsted acid-Bronsted base organocatalyst
Asymmetric cross aldol addition of isatins with α,β-unsaturated ketones catalyzed by a bifunctional Bronsted acid-Bronsted base organocatalyst
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DOI：
10.1016/j.tet.2012.03.042
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发表时间：
2012-05-20
期刊：
影响因子：
2.1
通讯作者：
Wang, Xing-Wang
中科院分区：
文献类型：
--
作者：
Liu, Guo-Gui;Zhao, Hua;Wang, Xing-Wang
在金鸡纳生物碱衍生的双功能Bronsted酸-Bronsted碱催化剂催化下，靛红与α，β-不饱和酮发生了不对称交叉羟醛缩合反应，得到了中等至良好产率（18-98%）和中等至良好的对映选择性（30-97%）的羟醛加成物。非共价有机催化的不对称交叉羟醛缩合反应显示了广泛的底物范围和广泛的官能团耐受性，尽管两个反应伙伴的电子和空间性质对反应性和立体控制有相当大的和规律的影响。(C)2012爱思唯尔有限公司保留所有权利。
The asymmetric cross-aldol reaction of isatins with alpha,beta-unsaturated ketones has been developed under catalysis by a Cinchona alkaloid-derivated bifunctional Bronsted acid-Bronsted base catalyst, affording the aldol adducts in moderate to good yields (18-98%) with moderate to good enantioselectivities (30-97%). The noncovalent organo-catalyzed asymmetric cross-aldol reaction displays a broad substrate scope and wide functional-group tolerability, albeit the electronic and steric properties of both reaction partners have considerable and regular effects on the reactivity and stereocontrol. (C) 2012 Elsevier Ltd. All rights reserved.