Organocatalytic enantioselective olefin aminofluorination.
Chiral beta-fluoroamines are increasingly prevalent in medicinal compounds, but there are few efficient methods to access them from achiral starting materials. To address this, a multicomponent organocascade reaction was developed in which chiral alpha-fluoro-beta-amino aldehydes were generated in a single flask from achiral alpha,beta-unsaturated aldehydes (2), using catalyst 12a. Conversions up to 85%, dr's up to 98:2 and ee's up to 99% of the corresponding alcohol (9) were achieved in this reaction.
Appayee
Chandrakumar
C
Department of Chemistry, Brooklyn College and the City University of New York, 2900 Bedford Avenue, Brooklyn, New York 11210, USA.
Brenner-Moyer
Stacey E
SE
D000447:Aldehydes / Q000737:chemistry*; D000475:Alkenes / Q000737:chemistry*; D000588:Amines / Q000737:chemistry*; D002384:Catalysis; D020650:Combinatorial Chemistry Techniques; D054879:Halogenation; D015394:Molecular Structure; D013237:Stereoisomerism
D000447:Aldehydes; D000475:Alkenes; D000588:Amines