title: Regiodivergent addition of phenols to allylic oxides: control of 1,2- and 1,4-additions for cyclitol synthesis.
abstract: Control of 1,2- and 1,4-addition of substituted phenols to allylic oxides is achieved by intercepting palladium π-allyl complexes. The interconversion of palladium complexes results in the total synthesis of MK 7607, cyathiformine B type, streptol, and a new cyclitol.
authors.affiliation: Department of Chemistry and Chemical Biology, Cornell University, 259 East Ave., Ithaca, NY 14853 (USA).
authors.forename: Matthew J
authors.initials: MJ
authors.lastname: Moschitto
authors.forename: David N
authors.initials: DN
authors.lastname: Vaccarello
authors.forename: Chad A
authors.initials: CA
authors.lastname: Lewis
mesh_terms: D000498:Allyl Compounds / Q000737:chemistry*; D002384:Catalysis; D054812:Cyclitols / Q000138:chemical synthesis* / Q000737:chemistry; D010087:Oxides / Q000737:chemistry*; D010165:Palladium / Q000737:chemistry; D010636:Phenols / Q000737:chemistry*; D013237:Stereoisomerism
chemical_list: D000498:Allyl Compounds; D054812:Cyclitols; D010087:Oxides; D010636:Phenols; D010165:Palladium
keywords: carbasugars; homogeneous catalysis; palladium; regiodivergence; synthetic methods