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The proline-catalyzed direct asymmetric three-component Mannich reaction: scope, optimization, and application to the highly enantioselective synthesis of 1,2-amino alcohols.
Journal of the American Chemical Society ( IF 15.0 ) Pub Date : 2002 Feb 6
List, Benjamin, Pojarliev, Peter, Biller, William T, Martin, Harry J

We have developed proline-catalyzed direct asymmetric three-component Mannich reactions of ketones, aldehydes, and amines. Several of the studied reactions provide beta-amino carbonyl compounds (Mannich products) in excellent enantio-, diastereo-, regio-, and chemoselectivities. The scope of each of the three components and the influence of the catalyst structure on the reaction are described. Reaction conditions have been optimized, and the mechanism and source of asymmetric induction are discussed. We further present application of our reaction to the highly enantioselective synthesis of 1,2-amino alcohols.

中文翻译:

脯氨酸催化的直接不对称三组分曼尼希反应:范围,优化和在1,2-氨基醇的高对映选择性合成中的应用。

我们已经开发了脯氨酸催化的酮,醛和胺的直接不对称三组分曼尼希反应。几个已研究的反应提供了对映体,非对映体,区域和化学选择性优异的β-氨基羰基化合物(曼尼希产品)。描述了三种组分各自的范围以及催化剂结构对反应的影响。优化了反应条件,并讨论了不对称诱导的机理和来源。我们进一步介绍了我们的反应在1,2-氨基醇的高度对映选择性合成中的应用。
更新日期:2017-01-31
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