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J Am Chem Soc ; 124(5): 827-33, 2002 Feb 06.
Article in English | MEDLINE | ID: mdl-11817958

ABSTRACT

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.


Subject(s)
Amino Alcohols/chemistry , Proline/chemistry , Aldehydes/chemistry , Amines/chemistry , Catalysis , Ketones/chemistry , Mannich Bases/chemistry , Stereoisomerism , Substrate Specificity
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