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. 2012 Jun 27;134(25):10389-92.
doi: 10.1021/ja304095z. Epub 2012 Jun 14.

Highly enantioselective electrophilic α-bromination of enecarbamates: chiral phosphoric acid and calcium phosphate salt catalysts

Aurélien Alix  1 , Claudia Lalli, Pascal Retailleau, Géraldine Masson
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Highly enantioselective electrophilic α-bromination of enecarbamates: chiral phosphoric acid and calcium phosphate salt catalysts

Aurélien Alix et al. J Am Chem Soc. .

Abstract

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.

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