title: Synthesis of substituted 3-hydroxy-2-furanone derivatives via an unusual enolate Wittig rearrangement/alkylative cyclization sequence.
abstract: Treatment of methyl O-(alkynylmethyl) glycolate derivatives with dialkylboron triflates and Hünig's base leads to the formation of highly substituted 3-hydroxy-2-furanone derivatives. The transformations appear to proceed via an unusual mechanism involving initial 2,3-Wittig rearrangement of a boron ester enolate followed by an alkylative cyclization reaction that leads to incorporation of an alkyl group from the boron reagent into the product.
authors.affiliation: Department of Chemistry, University of Michigan , 930 North University Avenue, Ann Arbor, Michigan, 48109-1055, United States.
authors.forename: Renata K
authors.initials: RK
authors.lastname: Everett
authors.forename: John P
authors.initials: JP
authors.lastname: Wolfe