N-heterocyclic carbene gold(I) catalyzed transformation of N-tethered 1,5-bisallenes to 6,7-dimethylene-3-azabicyclo[3.1.1]heptanes.
Tying up loose ends: The reaction of bisallenes tethered with N-(p-tolylsulfonamide) in the presence of a cationic gold N-heterocyclic carbene catalyst gave new cycloisomerization products, 6,7-dimethyleneazabicyclo[3.1.1]heptanes, in high yields (see scheme; IPr = N,N'-bis(2,6-diisopropylphenyl)imidazol-2-ylidene).
Kim
Soo Min
SM
Intelligent Textile System Research Center, Department of Chemistry, College of Natural Sciences, Seoul National University, Seoul 151-747, Korea.
Park
Ji Hoon
JH
Kang
Youn Kyung
YK
Chung
Young Keun
YK
D000466:Alkadienes / Q000737:chemistry*; D053961:Azabicyclo Compounds / Q000138:chemical synthesis / Q000737:chemistry*; D002384:Catalysis; D003500:Cyclization; D006046:Gold / Q000737:chemistry*; D007536:Isomerism; D008697:Methane / Q000031:analogs & derivatives* / Q000737:chemistry
D000466:Alkadienes; D053961:Azabicyclo Compounds; C030011:carbene; C025947:propadiene; D006046:Gold; D008697:Methane