title: Nitrile ylides: diastereoselective cycloadditions using chiral oxazolidinones without Lewis acid.
abstract: Lewis acid complexation is generally required for chiral-auxiliary-controlled stereoselectivity, and chiral Lewis acid catalysis is frequently optimal for introducing asymmetry. In this work, we show that nitrile ylide cycloadditions to electron-poor acceptors attached to chiral auxiliaries proceed in high yield and stereoselectivity in the absence of Lewis acids. In contrast, chiral Lewis acids are inferior in these cycloadditions.
authors.affiliation: Department of Chemistry and Molecular Biology, North Dakota State University, NDSU Department 2735, PO Box 6050, Fargo, North Dakota 58108-6050, USA. mukund.sibi@ndsu.edu
authors.forename: Mukund P
authors.initials: MP
authors.lastname: Sibi
authors.forename: Takahiro
authors.initials: T
authors.lastname: Soeta
authors.forename: Craig P
authors.initials: CP
authors.lastname: Jasperse
mesh_terms: D000143:Acids / Q000737:chemistry; D002384:Catalysis; D018360:Crystallography, X-Ray; D003500:Cyclization; D008956:Models, Chemical; D015394:Molecular Structure; D009570:Nitriles / Q000737:chemistry*; D023303:Oxazolidinones / Q000737:chemistry*; D013237:Stereoisomerism
chemical_list: D000143:Acids; D009570:Nitriles; D023303:Oxazolidinones