The Proline-Catalyzed Direct Asymmetric Three-Component Mannich Reaction:  Scope, Optimization, and Application to the Highly Enantioselective Synthesis of 1,2-Amino Alcohols

We have developed proline-catalyzed direct asymmetric three-component Mannich reactions of ketones, aldehydes, and amines. Several of the studied reactions provide β-amino carbonyl compounds (Mannich products) in excellent enantio-, diastereo-, regio-, and chemoselectivities. The scope of each of th...

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Bibliographic Details
Published in:Journal of the American Chemical Society 2002-02, Vol.124 (5), p.827-833
Main Authors: List, Benjamin, Pojarliev, Peter, Biller, William T, Martin, Harry J
Format: Article
Language:English
Subjects:
Aldehydes - chemistry
Amines - chemistry
Amino Alcohols - chemistry
Catalysis
Chemistry
Exact sciences and technology
Ketones - chemistry
Mannich Bases - chemistry
Organic chemistry
Proline - chemistry
Stereoisomerism
Substrate Specificity
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Summary:We have developed proline-catalyzed direct asymmetric three-component Mannich reactions of ketones, aldehydes, and amines. Several of the studied reactions provide β-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.
ISSN:0002-7863
1520-5126
DOI:10.1021/ja0174231