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

List, Benjamin; Pojarliev, Peter; Biller, William T.; Martin, Harry J.

doi:10.1021/ja0174231

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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

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List, B., Pojarliev, P., Biller, W. T., & Martin, H. J. (2002). 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, 124(5), 827-833. doi:10.1021/ja0174231.

Cite as: https://hdl.handle.net/11858/00-001M-0000-0014-A4CF-8

Abstract

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.