Regio-, Diastereo-, and Enantioselective Nitroso-Diels–Alder Reaction of 1,3-Diene-1-carbamates Catalyzed by Chiral Phosphoric Acids - Archive ouverte HAL Accéder directement au contenu
Article Dans Une Revue Journal of the American Chemical Society Année : 2015

Regio-, Diastereo-, and Enantioselective Nitroso-Diels–Alder Reaction of 1,3-Diene-1-carbamates Catalyzed by Chiral Phosphoric Acids

Résumé

Chiral phosphoric acid-catalyzed asymmetric nitroso-Diels–Alder reaction of nitrosoarenes with carbamate-dienes afforded cis-3,6-disubstituted dihydro-1,2-oxazines in high yields with excellent regio-, diastereo-, and enantioselectivities. Interestingly, we observed that the catalyst is able not only to control the enantioselectivity but also to reverse the regioselectivity of the noncatalyzed nitroso-Diels–Alder reaction. The regiochemistry reversal and asynchronous concerted mechanism were confirmed by DFT calculations
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hal-03161977 , version 1 (27-03-2023)

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Jonathan Pous, Thibaut Courant, Guillaume Bernadat, Bogdan Iorga, Florent Blanchard, et al.. Regio-, Diastereo-, and Enantioselective Nitroso-Diels–Alder Reaction of 1,3-Diene-1-carbamates Catalyzed by Chiral Phosphoric Acids. Journal of the American Chemical Society, 2015, 137 (37), pp.11950-11953. ⟨10.1021/jacs.5b08515⟩. ⟨hal-03161977⟩
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