Organocatalytic asymmetric alpha-bromination of aldehydes and ketones.
The first organocatalytic enantioselective alpha-bromination of aldehydes and ketones is presented; a C2-symmetric diphenylpyrrolidine catalyst afforded the alpha-brominated aldehydes in good yields and up to 96% ee, while ketones were alpha-brominated by a C2-symmetric imidazolidine in up to 94% ee; furthermore, the organocatalytic enantioselective alpha-iodination of aldehydes is also demonstrated to proceed with up to 89% ee.
Bertelsen
Søren
S
Danish National Research Foundation: Center for Catalysis, Department of Chemistry, Aarhus University.
Halland
Nis
N
Bachmann
Stephan
S
Marigo
Mauro
M
Braunton
Alan
A
Jørgensen
Karl Anker
KA
D000447:Aldehydes / Q000737:chemistry*; D001966:Bromine / Q000737:chemistry*; D002384:Catalysis; D048289:Imidazolidines / Q000737:chemistry*; D007659:Ketones / Q000737:chemistry*; D015394:Molecular Structure; D011759:Pyrrolidines / Q000737:chemistry*; D013237:Stereoisomerism
D000447:Aldehydes; D048289:Imidazolidines; D007659:Ketones; D011759:Pyrrolidines; D001966:Bromine