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Organocatalytic Strategies for the Construction of Optically Active Imidazoles, Oxazoles, and Thiazoles
Author(s) -
Albrecht Łukasz,
Ransborg Lars Krogager,
Albrecht Anna,
Lykke Lennart,
Jørgensen Karl Anker
Publication year - 2011
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.201101817
Subject(s) - enantioselective synthesis , annulation , chemistry , catalysis , organocatalysis , combinatorial chemistry , optically active , cascade , organic chemistry , reaction conditions , chromatography
This study demonstrates the first enantioselective synthesis of hydroxyalkyl‐ and aminoalkyl‐substituted imidazoles, oxazoles, and thiazoles. The approach developed utilizes a highly effective one‐pot reaction cascade that consists of either an organocatalytic epoxidation or aziridination of α,β‐unsaturated aldehydes coupled with a [3+2]‐annulation, in which amidines, ureas, or thioureas act as effective 1,3‐dinucleophilic species. The methodology described benefits from low catalyst loadings, commercially and readily available starting materials, and mild reaction conditions.