Tungsten-catalyzed regioselective and stereospecific ring opening of 2,3-epoxy alcohols and 2,3-epoxy sulfonamides.
The first catalytic, highly C3-selective, stereosepecific ring-opening reaction of 2,3-epoxy alcohols and 2,3-epoxy sulfonamides has been accomplished. This process was efficiently promoted by W-salts, and the developed method was applicable to various epoxides with diverse N- and O-nucleophiles affording the products in good to excellent yields (up to 95%) and generally with high regioselectivities (C3:C2 up to >99:1).
Department of Chemistry, The University of Chicago , 5735 South Ellis Avenue, Chicago, Illinois 60637, United States.
Chuan
C
Wang
Hisashi
H
Yamamoto
D000438:Alcohols / Q000737:chemistry*; D002384:Catalysis; D004852:Epoxy Compounds / Q000737:chemistry*; D013237:Stereoisomerism; D013449:Sulfonamides / Q000737:chemistry*; D014414:Tungsten / Q000737:chemistry*
D000438:Alcohols; D004852:Epoxy Compounds; D013449:Sulfonamides; D014414:Tungsten