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Functionalized α,α-Dibromo Esters through Claisen Rearrangements of Dibromoketene Acetals

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journal contribution
posted on 20.02.2015, 00:00 by Nathan J. Dupper, Ohyun Kwon
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.