Chiral Brønsted acid-catalyzed asymmetric trisubstituted aziridine synthesis using α-diazoacyl oxazolidinones.
ABSTRACT Despite the remarkable advances in catalytic asymmetric aziridinations over the past decades, establishing a general procedure for the stereoselective synthesis of trisubstituted aziridines has remained an elusive goal. Chiral N-triflyl phosphoramide-catalyzed reactions of N-α-diazoacyl oxazolidinones and N-Boc imines were developed as a solution to this unmet challenge.
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ABSTRACT: A new chiral Brønsted acid-catalyzed aza-Diels-Alder reaction of cyclic C-acylimines with cyclopentadiene has been developed. The reaction provides optically active aza-tetracycles in good yields with high diastereo- and enantioselectivities under mild reaction conditions.Beilstein Journal of Organic Chemistry 01/2012; 8:1819-24. · 2.80 Impact Factor