Lewis acid catalyzed [1,3]-sigmatropic rearrangement of vinyl aziridines.
This paper details the copper-catalyzed ring expansion of vinyl aziridines to 3-pyrrolines. Broad substrate scope (24 examples) using tosyl- and phthalimide-protected vinyl aziridine substrates is observed. Cu(hfacac)2 was determined to be superior to all other catalysts tested.
Brichacek
Matthew
M
Department of Chemistry and Chemical Biology, Baker Laboratory, Cornell University, Ithaca, New York 14853-1301, USA.
Lee
Dongeun
D
Njardarson
Jon T
JT
D000143:Acids / Q000737:chemistry*; D001388:Aziridines / Q000138:chemical synthesis* / Q000737:chemistry; D002384:Catalysis; D003300:Copper / Q000737:chemistry; D007700:Kinetics; D015394:Molecular Structure; D011758:Pyrroles / Q000138:chemical synthesis / Q000737:chemistry; D014753:Vinyl Compounds / Q000138:chemical synthesis* / Q000737:chemistry
D000143:Acids; D001388:Aziridines; D011758:Pyrroles; D014753:Vinyl Compounds; C013231:pyrroline; C033132:aziridine; D003300:Copper