title: Expedient synthesis of chiral oxazolidinone scaffolds via rhodium-catalyzed asymmetric ring-opening with sodium cyanate.
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).
authors: Davenport Research Laboratories, Department of Chemistry, University of Toronto, 80 St. George Street, Toronto, Ontario, Canada M5S 3H6.
authors: Gavin Chit
authors: GC
authors: Tsui
authors: Nina M
authors: NM
authors: Ninnemann
authors: Akihito
authors: A
authors: Hosotani
authors: Mark
authors: M
authors: Lautens
mesh_terms: D002384:Catalysis; D003485:Cyanates / Q000737:chemistry*; D015394:Molecular Structure; D023303:Oxazolidinones / Q000138:chemical synthesis* / Q000737:chemistry; D012238:Rhodium / Q000737:chemistry*; D013237:Stereoisomerism
chemical_list: D003485:Cyanates; D023303:Oxazolidinones; C009281:sodium cyanate; D012238:Rhodium