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.
Department of Chemistry and Chemical Biology, Baker Laboratory, Cornell University, Ithaca, New York 14853-1301, USA.
Matthew
M
Brichacek
Dongeun
D
Lee
Jon T
JT
Njardarson
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