Synthetic studies and mechanistic insight in nickel-catalyzed [4+2+1] cycloadditions.
A new nickel-catalyzed procedure for the [4+2+1] cycloaddition of (trimethylsilyl)diazomethane with alkynes tethered to dienes has been developed. A broad range of unsaturated substrates participate in the sequence, and stereoselectivities are generally excellent. Stereochemical studies provided evidence for a mechanism that involves the [3,3] sigmatropic rearrangement of divinylcyclopropanes.
Ni
Yike
Y
Department of Chemistry, Wayne State University, Detroit, Michigan 48202-3489, USA.
Montgomery
John
J
D000475:Alkenes / Q000737:chemistry*; D000480:Alkynes / Q000737:chemistry*; D001952:Bridged-Ring Compounds / Q000138:chemical synthesis*; D002384:Catalysis; D003500:Cyclization; D003978:Diazomethane / Q000031:analogs & derivatives* / Q000737:chemistry; D009532:Nickel / Q000737:chemistry; D013237:Stereoisomerism; D014297:Trimethylsilyl Compounds / Q000737:chemistry*
C451480:(trimethylsilyl)diazaomethane; D000475:Alkenes; D000480:Alkynes; D001952:Bridged-Ring Compounds; D014297:Trimethylsilyl Compounds; D003978:Diazomethane; D009532:Nickel