Highly Enantioselective Electrophilic α-Bromination of Enecarbamates: Chiral Phosphoric Acid and Calcium Phosphate Salt Catalysts. - Archive ouverte HAL Accéder directement au contenu
Article Dans Une Revue Journal of the American Chemical Society Année : 2012

Highly Enantioselective Electrophilic α-Bromination of Enecarbamates: Chiral Phosphoric Acid and Calcium Phosphate Salt Catalysts.

Aurélien Alix
Claudia Lalli

Résumé

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.

Domaines

Chimie organique
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Dates et versions

hal-00722061 , version 1 (31-07-2012)

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Citer

Aurélien Alix, Claudia Lalli, Pascal Retailleau, Géraldine Masson. Highly Enantioselective Electrophilic α-Bromination of Enecarbamates: Chiral Phosphoric Acid and Calcium Phosphate Salt Catalysts.. Journal of the American Chemical Society, 2012, 134 (25), pp.10389-10392. ⟨10.1021/ja304095z⟩. ⟨hal-00722061⟩
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