Organocatalytic strategies for the construction of optically active imidazoles, oxazoles, and thiazoles.
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.
Center for Catalysis, Department of Chemistry, Aarhus University, 8000 Aarhus C, Denmark.
Łukasz
Ł
Albrecht
Lars Krogager
LK
Ransborg
Anna
A
Albrecht
Lennart
L
Lykke
Karl Anker
KA
Jørgensen