title: Functionalized α,α-dibromo esters through Claisen rearrangements of dibromoketene acetals.
abstract: Allylic alcohols can be transformed into γ,δ-unsaturated α,α-dibromo esters through a two-step process: formation of a bromal-derived mixed acetal, followed by tandem dehydrobromination/Claisen rearrangement. The scope and selectivity of both steps have been investigated. The product α,α-dibromo esters were subjected to various carbon-carbon bond-forming reactions, oxidations, and lactonizations.
authors: Department of Chemistry and Biochemistry, University of California , Los Angeles, 607 Charles E. Young Drive East, Los Angeles, California 90095-1569, United States.
authors: Nathan J
authors: NJ
authors: Dupper
authors: Ohyun
authors: O
authors: Kwon
mesh_terms: D000080:Acetals / Q000737:chemistry*; D004952:Esters; D005030:Ethylenes / Q000737:chemistry*; D006842:Hydrocarbons, Brominated / Q000138:chemical synthesis* / Q000737:chemistry; D007659:Ketones / Q000737:chemistry*; D015394:Molecular Structure; D020005:Propanols / Q000737:chemistry*; D013237:Stereoisomerism
chemical_list: D000080:Acetals; D004952:Esters; D005030:Ethylenes; D006842:Hydrocarbons, Brominated; D007659:Ketones; D020005:Propanols; C006463:allyl alcohol; C008223:ketene