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Updated: Jan 25, 2026

Enzymatic Synthesis of Epoxidized Metabolites of Docosahexaenoic, Eicosapentaenoic, and Arachidonic Acids
Published on: June 28, 2019
Selective C-C Coupling of Vinyl Epoxides with Diborylmethide Lithium Salts
Riccardo Gava1, Elena Fernández1
1Department Química Física i Inorgànica, University Rovira i Virgili, Tarragona, Spain.
Abstract:
Vinyl epoxides and styrene oxide can react with diborylmethide lithium salts through an exclusive SN 2 borylmethylation/ring opening in a regio- and diastereoselective way, depending on the nature of the substrate. The ring-opening protocol provides homoallylboronates that can be transformed into challenging diastereomeric bishomoallylic alicyclic 1,3-diols. Unprecedented 3-borylated 1,2-oxaborolan-2-ol products were prepared by borylmethylation/ring opening of 2-methyl-2-vinyloxirane followed by intramolecular cyclization.
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