Regio-, Diastereo-, and Enantioselective Nitroso-Diels-Alder Reaction of 1,3-Diene-1-carbamates Catalyzed by Chiral Phosphoric Acids.
J Am Chem Soc
; 137(37): 11950-3, 2015 Sep 23.
Article
em En
| MEDLINE
| ID: mdl-26355670
ABSTRACT
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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Base de dados:
MEDLINE
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Ácidos Fosfóricos
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Carbamatos
Idioma:
En
Ano de publicação:
2015
Tipo de documento:
Article