Lewis acid-catalyzed [3 + 2]cyclo-addition of alkynes with N-tosyl-aziridines via carbon-carbon bond cleavage: synthesis of highly substituted 3-pyrrolines.
A novel, efficient, and highly regioselective Lewis acid-catalyzed [3 + 2] cycloaddition of alkynes with azomethine ylides, which are easily obtained from N-tosylaziridines via C-C bond heterolysis at room temperature was developed. Moderate enantioselectivity (70% ee) can be achieved by the application of the commercially available chiral Pybox 7 as the ligand.
Shanghai Key Laboratory of Green Chemistry and Chemical Processes, Department of Chemistry, East China Normal University, 3663 N. Zhongshan Road, Shanghai 200062, PR China.
Lei
L
Li
Junliang
J
Zhang
D000480:Alkynes / Q000737:chemistry*; D001388:Aziridines / Q000737:chemistry*; D002244:Carbon / Q000737:chemistry; D002384:Catalysis; D003500:Cyclization; D058116:Lewis Acids / Q000737:chemistry*; D015394:Molecular Structure; D011758:Pyrroles / Q000737:chemistry*; D013237:Stereoisomerism
D000480:Alkynes; D001388:Aziridines; D058116:Lewis Acids; D011758:Pyrroles; C013231:pyrroline; D002244:Carbon