title: Lewis acid-catalyzed formal [3+2] cycloadditions of N-tosyl aziridines with electron-rich alkenes via selective carbon-carbon bond cleavage.
abstract: A novel, mild, robust catalyst Y(OTf)(3) for C-C bond heterolysis of N-tosyl aziridines was developed and the resulting metallo-azomethine ylides may readily undergo [3+2] dipolar cycloaddition with an electron-rich olefin via a stepwise reaction pathway with high regio- and diastereoselectivity leading to substituted pyrrolidines.
authors: Shanghai Key Laboratory of Green Chemistry and Chemical Processes, Department of Chemistry, East China Normal University, 3663 N. Zhongshan Road, Shanghai 200062, China.
authors: Lei
authors: L
authors: Li
authors: Xingxing
authors: X
authors: Wu
authors: Junliang
authors: J
authors: Zhang
mesh_terms: D000475:Alkenes / Q000737:chemistry; D001388:Aziridines / Q000138:chemical synthesis*; D001391:Azo Compounds / Q000737:chemistry; D001688:Biological Products; D002244:Carbon / Q000737:chemistry; D002384:Catalysis; D003500:Cyclization; D004583:Electrons; D058116:Lewis Acids / Q000737:chemistry; D011759:Pyrrolidines / Q000138:chemical synthesis*; D013237:Stereoisomerism; D013882:Thiosemicarbazones / Q000737:chemistry
chemical_list: D000475:Alkenes; D001388:Aziridines; D001391:Azo Compounds; D001688:Biological Products; D058116:Lewis Acids; D011759:Pyrrolidines; D013882:Thiosemicarbazones; C512188:azomethine; D002244:Carbon