Organocatalytic regio- and enantioselective formal [4 + 2]-annulation of chiral nitrogen-containing dipoles

Abstract

Quinidine-catalyzed regio- and enantioselective formal [4 + 2]-cycloadditions of 2-(4H-benzo[d][1,3]oxazin-4-yl)acrylates with N-tosyl-2-methylenebut-3-enoates and 2-methylene-3-oxoalkanoates have been developed for the first time. The reaction features the in situ formation of chiral nitrogen-containing dipolar intermediates, a ring-opening/Michael addition/annulation cascade reaction, and works well over a broad substrate scope to furnish the tetrahydroquinolines in high yields with high asymmetric induction under mild conditions.

Keywords

Annulation / benzoxazine / diene / organocatalysis / tetrahydroquinoline

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