Organocatalytic Asymmetric Allylic Benzylborylation via Fluoride-Assisted Catalytic Generation of α‑Boryl Carbanionic Intermediates

Herein we describe the organocatalytic asymmetric allylic benzylborylation of allyl fluorides with α-silyl benzylboronic esters. The catalytic protocol leverages the singular features of fluoride as an unconventional leaving group, enabling the catalytic generation of reactive α-boryl carbanion spec...

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Bibliographic Details
Published inOrganic letters Vol. 26; no. 39; pp. 8394 - 8399
Main Authors Duran, Jordi, Rodríguez, Paula, Vermeer, Ward, Companyó, Xavier
Format Journal Article
LanguageEnglish
Published United States American Chemical Society 04.10.2024
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Letter
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Summary:Herein we describe the organocatalytic asymmetric allylic benzylborylation of allyl fluorides with α-silyl benzylboronic esters. The catalytic protocol leverages the singular features of fluoride as an unconventional leaving group, enabling the catalytic generation of reactive α-boryl carbanion species through desilylative activation. It allows the construction of a wide set of homoallylic benzylated organoboronates bearing two contiguous stereocenters. The chiral boronate installed in the products serves as a synthetic lynchpin to construct complex chemical architectures in a stereospecific manner.
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ISSN:1523-7060
1523-7052
1523-7052
DOI:10.1021/acs.orglett.4c03242