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Organic letters

Expedient synthesis of chiral oxazolidinone scaffolds via rhodium-catalyzed asymmetric ring-opening with sodium cyanate.


PMID 23394120

Abstract

A method for synthesizing chiral oxazolidinone scaffolds from readily available oxabicyclic alkenes is described. The reaction utilizes a domino sequence of Rh(I)-catalyzed asymmetric ring-opening (ARO) with sodium cyanate as a novel nucleophile followed by intramolecular cyclization to generate oxazolidinone products in excellent enantioselectivities (trans stereochemistry).