Highly enantioselective electrophilic α-bromination of enecarbamates: chiral phosphoric acid and calcium phosphate salt catalysts.
Metal-free chiral phosphoric acids and chiral calcium phosphates both catalyze highly enantio- and diastereoselective electrophilic α-bromination of enecarbamates to provide an atom-economical synthesis of enantioenriched vicinal haloamines. Either enantiomer can be formed in good yield with excellent diastereo- and enantioselectivity simply by switching the catalyst from a phosphoric acid to its calcium salt.
Centre de Recherche de Gif, Institut de Chimie des Substances Naturelles, CNRS, 91198 Gif-sur-Yvette Cedex, France.
Aurélien
A
Alix
Claudia
C
Lalli
Pascal
P
Retailleau
Géraldine
G
Masson
D000475:Alkenes / Q000737:chemistry*; D002130:Calcium Phosphates / Q000737:chemistry*; D002219:Carbamates / Q000737:chemistry*; D002384:Catalysis; D054879:Halogenation; D015394:Molecular Structure; D013237:Stereoisomerism
D000475:Alkenes; D002130:Calcium Phosphates; D002219:Carbamates; C020243:calcium phosphate