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Acyclic Chiral Amines and Amino Acids as Inexpensive and Readily Tunable Catalysts for the Direct Asymmetric Three‐Component Mannich Reaction
Author(s) -
Ibrahem Ismail,
Zou Weibiao,
Engqvist Magnus,
Xu Yongmei,
Córdova Armando
Publication year - 2005
Publication title -
chemistry – a european journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.687
H-Index - 242
eISSN - 1521-3765
pISSN - 0947-6539
DOI - 10.1002/chem.200500746
Subject(s) - mannich reaction , chemistry , amino acid , catalysis , enantioselective synthesis , alanine , organocatalysis , organic chemistry , valine , stereoselectivity , serine , tetrazole , component (thermodynamics) , combinatorial chemistry , enzyme , biochemistry , physics , thermodynamics
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.