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oai:recercat.cat:2445/2227312025-12-04T21:43:54Zcom_2072_1057col_2072_478917col_2072_478933

urn:hdl:2445/222731 Organocatalytic Asymmetric Allylic Benzylborylation via Fluoride-Assisted Catalytic Generation of α-Boryl Carbanionic Intermediates Duran, Jordi Rodríguez, Paula Vermeer, Ward Companyó Montaner, Xavier Compostos orgànics Anions Estructura molecular Organic compounds Anions Molecular structure 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. 2025-07-31T12:44:25Z 2025-07-31T12:44:25Z 2024-10-04 2025-07-31T12:44:25Z info:eu-repo/semantics/article info:eu-repo/semantics/publishedVersion Reproducció del document publicat a: https://doi.org/10.1021/acs.orglett.4c03242 Organic Letters, 2024, vol. 26, num.39, p. 8394-8399 https://doi.org/10.1021/acs.orglett.4c03242 cc-by (c) Duran, Jordi et al., 2024 http://creativecommons.org/licenses/by/3.0/es/ info:eu-repo/semantics/openAccess American Chemical Society Articles publicats en revistes (Química Inorgànica i Orgànica)