Nitrile ylides: diastereoselective cycloadditions using chiral oxazolidinones without Lewis acid.
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.
Sibi
Mukund P
MP
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
Soeta
Takahiro
T
Jasperse
Craig P
CP
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
D000143:Acids; D009570:Nitriles; D023303:Oxazolidinones