Gold(I)-catalyzed cascade cyclization of allenyl epoxides.
Cationic gold(I) phosphite catalysts activate allenes for epoxide cascade reactions. The system is tolerant of numerous functional groups (sulfones, esters, ethers, sulfonamides) and proceeds at room temperature in dichloromethane. The cyclization pathway is sensitive to the substitution pattern of the epoxide and the backbone structure of the A-ring. It is capable of producing medium-ring ethers, fused 6-5 bicyclic, and linked pyran-furan structures. The resulting cycloisomers are reminiscent of structures found in numerous polyether natural products.
Tarselli
Michael A
MA
Caudill Laboratories, University of North Carolina at Chapel Hill, Chapel Hill, North Carolina 27599-3290, USA.
Zuccarello
J Lucas
JL
Lee
Stephen J
SJ
Gagné
Michel R
MR
D000466:Alkadienes / Q000737:chemistry*; D002384:Catalysis; D018360:Crystallography, X-Ray; D003500:Cyclization; D004852:Epoxy Compounds / Q000737:chemistry*; D006046:Gold / Q000737:chemistry*; D008752:Methylene Chloride / Q000737:chemistry; D011714:Pyrans / Q000737:chemistry
D000466:Alkadienes; D004852:Epoxy Compounds; D011714:Pyrans; C025947:propadiene; D008752:Methylene Chloride; D006046:Gold