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

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

Organic letters (2013-02-12)
Gavin Chit Tsui, Nina M Ninnemann, Akihito Hosotani, Mark Lautens
RESUMO

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).

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Sigma-Aldrich
Rhodium, powder, 99.95% trace metals basis
Sigma-Aldrich
Sodium cyanate, 96%