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Facial selectivity induced by N-aryl atropisomerism in benzonitrile oxide cycloadditions with 4-methylene-2-oxazolidinones†
Sarah L. Harding,G. Paul Savage
Organic & Biomolecular Chemistry Pub Date : 04/18/2012 00:00:00 , DOI:10.1039/C2OB25271F
Abstract

N-Aryl 4-methylene-2-oxazolidinones, prepared via the corresponding O-propargyl carbamates, underwent nitrile oxide cycloaddition with benzonitrile oxide to give 5-spiro isoxazoline adducts with complete regioselectivity. Steric hindrance by atropisomerism around the N-aryl bond induced facial selectivity in these cycloadditions.

Graphical abstract: Facial selectivity induced by N-aryl atropisomerism in benzonitrile oxide cycloadditions with 4-methylene-2-oxazolidinones
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