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Enantioselective addition of aldehydes to amines via combined catalytic biomimetic oxidation and organocatalytic C-C- bond formation
Journal article   Peer reviewed

Enantioselective addition of aldehydes to amines via combined catalytic biomimetic oxidation and organocatalytic C-C- bond formation

Ismail ibrahem, Joseph S M Samec, Jan-E Bäckvall and Armando Córdiva
Tetrahedron letters, Vol.46(23), pp.3965-3968
06/06/2005
DOI: https://doi.org/10.1016/j.tetlet.2005.04.047

Abstract

Biomimetic oxidation; Catalysis; Asymmetric synthesis; Ruthenium; Proline Chemical Sciences Chemistry Kemi Natural Sciences Naturvetenskap Organic Chemistry Organisk kemi
The biomimetic catalytic enantioselective addition of aldehydes to amines is reported. This was accomplished by combining biomimetic coupled catalytic aerobic oxidation of amines involving ruthenium-induced dehydrogenation and organocatalytic asymmetric Mannich reactions. The novel one-pot reactions furnished β-amino aldehyde and α-amino acid derivatives in high yields with excellent chemoselectivity and up to >99% ee.

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