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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.
J Am Chem Soc. 2002 Feb 06; 124(5):827-33.JA

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.

Authors+Show Affiliations

List B
Department of Molecular Biology, The Scripps Research Institute, 10550 North Torrey Pines Road, La Jolla, California 92037, USA. blist@scripps.edu
Pojarliev P
No affiliation info available
Biller WT
No affiliation info available
Martin HJ
No affiliation info available

MeSH

AldehydesAminesAmino AlcoholsCatalysisKetonesMannich BasesProlineStereoisomerismSubstrate Specificity

Pub Type(s)

Journal Article
Research Support, Non-U.S. Gov't

Language

eng

PubMed ID

11817958

Citation

List, Benjamin, et al. "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, vol. 124, no. 5, 2002, pp. 827-33.
List B, Pojarliev P, Biller WT, et al. The proline-catalyzed direct asymmetric three-component Mannich reaction: scope, optimization, and application to the highly enantioselective synthesis of 1,2-amino alcohols. J Am Chem Soc. 2002;124(5):827-33.
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), 827-33.
List B, et al. The Proline-catalyzed Direct Asymmetric Three-component Mannich Reaction: Scope, Optimization, and Application to the Highly Enantioselective Synthesis of 1,2-amino Alcohols. J Am Chem Soc. 2002 Feb 6;124(5):827-33. PubMed PMID: 11817958.
* Article titles in AMA citation format should be in sentence-case
TY - JOUR T1 - The proline-catalyzed direct asymmetric three-component Mannich reaction: scope, optimization, and application to the highly enantioselective synthesis of 1,2-amino alcohols. AU - List,Benjamin, AU - Pojarliev,Peter, AU - Biller,William T, AU - Martin,Harry J, PY - 2002/1/31/pubmed PY - 2002/4/6/medline PY - 2002/1/31/entrez SP - 827 EP - 33 JF - Journal of the American Chemical Society JO - J Am Chem Soc VL - 124 IS - 5 N2 - 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. SN - 0002-7863 UR - https://www.unboundmedicine.com/medline/citation/11817958/The_proline_catalyzed_direct_asymmetric_three_component_Mannich_reaction:_scope_optimization_and_application_to_the_highly_enantioselective_synthesis_of_12_amino_alcohols_ L2 - https://doi.org/10.1021/ja0174231 DB - PRIME DP - Unbound Medicine ER -