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Functionalized ?,?-dibromo esters through Claisen rearrangements of dibromoketene acetals.

ABSTRACT: Allylic alcohols can be transformed into ?,?-unsaturated ?,?-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 ?,?-dibromo esters were subjected to various carbon-carbon bond-forming reactions, oxidations, and lactonizations.

SUBMITTER: Dupper NJ 

PROVIDER: S-EPMC4482617 | biostudies-literature | 2015 Feb

REPOSITORIES: biostudies-literature

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Functionalized α,α-dibromo esters through Claisen rearrangements of dibromoketene acetals.

Dupper Nathan J NJ   Kwon Ohyun O  

Organic letters 20150211 4

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. ...[more]

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