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Stereodivergent Olefination of Enantioenriched Boronic Esters.

ABSTRACT: A stereodivergent coupling reaction between vinyl halides and boronic esters is described. This coupling process proceeds without a transition-metal catalyst, instead proceeding by electrophilic selenation or iodination of a vinyl boronate complex followed by stereospecific syn or anti elimination. Chiral, nonracemic boronic esters could be coupled with complete enantiospecificity. The process enables the highly stereoselective synthesis of either the E or Z alkene from a single isomer of a vinyl coupling partner.

SUBMITTER: Armstrong RJ

PROVIDER: S-EPMC5347846 | biostudies-literature | 2017 Jan

REPOSITORIES: biostudies-literature

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Stereodivergent Olefination of Enantioenriched Boronic Esters.

Armstrong Roly J RJ García-Ruiz Cristina C Myers Eddie L EL Aggarwal Varinder K VK

Angewandte Chemie (International ed. in English) 20161213 3

A stereodivergent coupling reaction between vinyl halides and boronic esters is described. This coupling process proceeds without a transition-metal catalyst, instead proceeding by electrophilic selenation or iodination of a vinyl boronate complex followed by stereospecific syn or anti elimination. Chiral, nonracemic boronic esters could be coupled with complete enantiospecificity. The process enables the highly stereoselective synthesis of either the E or Z alkene from a single isomer of a viny ...[more]

PMID: 27958668

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