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Acyclic chiral amines and amino acids as inexpensive and readily tunable catalysts for the direct asymmetric three-component Mannich reaction.
Chemistry. 2005 Nov 18; 11(23):7024-9.C

Abstract

The direct three-component asymmetric Mannich reaction catalyzed by acyclic chiral amines or amino acids is presented. Simple acyclic chiral amines and amino acids--such as alanine-tetrazole (9), alanine, valine, and serine-catalyzed the three-component asymmetric Mannich reactions between unmodified ketones, p-anisidine, and aldehydes with high chemo- and stereoselectivity, furnishing the corresponding Mannich bases with up to >99 % ee. This study demonstrates that the whole range of amino acids in nature, as well as nonproteogenic amino acid derivatives, can be considered in the design and tuning of novel, inexpensive organocatalysts for the direct asymmetric Mannich reaction.

Authors+Show Affiliations

Ibrahem I
Department of Organic Chemistry, Arrhenius Laboratory, Stockholm University, 106 91 Stockholm, Sweden.
Zou W
No affiliation info available
Engqvist M
No affiliation info available
Xu Y
No affiliation info available
Córdova A
No affiliation info available

MeSH

AminesAmino AcidsCatalysisChromatography, High Pressure LiquidMagnetic Resonance SpectroscopySpectrometry, Mass, Matrix-Assisted Laser Desorption-IonizationStereoisomerism

Pub Type(s)

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

Language

eng

PubMed ID

16189842

Citation

Ibrahem, Ismail, et al. "Acyclic Chiral Amines and Amino Acids as Inexpensive and Readily Tunable Catalysts for the Direct Asymmetric Three-component Mannich Reaction." Chemistry (Weinheim an Der Bergstrasse, Germany), vol. 11, no. 23, 2005, pp. 7024-9.
Ibrahem I, Zou W, Engqvist M, et al. Acyclic chiral amines and amino acids as inexpensive and readily tunable catalysts for the direct asymmetric three-component Mannich reaction. Chemistry. 2005;11(23):7024-9.
Ibrahem, I., Zou, W., Engqvist, M., Xu, Y., & Córdova, A. (2005). Acyclic chiral amines and amino acids as inexpensive and readily tunable catalysts for the direct asymmetric three-component Mannich reaction. Chemistry (Weinheim an Der Bergstrasse, Germany), 11(23), 7024-9.
Ibrahem I, et al. Acyclic Chiral Amines and Amino Acids as Inexpensive and Readily Tunable Catalysts for the Direct Asymmetric Three-component Mannich Reaction. Chemistry. 2005 Nov 18;11(23):7024-9. PubMed PMID: 16189842.
* Article titles in AMA citation format should be in sentence-case
TY - JOUR T1 - Acyclic chiral amines and amino acids as inexpensive and readily tunable catalysts for the direct asymmetric three-component Mannich reaction. AU - Ibrahem,Ismail, AU - Zou,Weibiao, AU - Engqvist,Magnus, AU - Xu,Yongmei, AU - Córdova,Armando, PY - 2005/9/29/pubmed PY - 2006/12/12/medline PY - 2005/9/29/entrez SP - 7024 EP - 9 JF - Chemistry (Weinheim an der Bergstrasse, Germany) JO - Chemistry VL - 11 IS - 23 N2 - The direct three-component asymmetric Mannich reaction catalyzed by acyclic chiral amines or amino acids is presented. Simple acyclic chiral amines and amino acids--such as alanine-tetrazole (9), alanine, valine, and serine-catalyzed the three-component asymmetric Mannich reactions between unmodified ketones, p-anisidine, and aldehydes with high chemo- and stereoselectivity, furnishing the corresponding Mannich bases with up to >99 % ee. This study demonstrates that the whole range of amino acids in nature, as well as nonproteogenic amino acid derivatives, can be considered in the design and tuning of novel, inexpensive organocatalysts for the direct asymmetric Mannich reaction. SN - 0947-6539 UR - https://www.unboundmedicine.com/medline/citation/16189842/Acyclic_chiral_amines_and_amino_acids_as_inexpensive_and_readily_tunable_catalysts_for_the_direct_asymmetric_three_component_Mannich_reaction_ DB - PRIME DP - Unbound Medicine ER -