Work

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

Year: 2024

Type: article

Abstract: 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.

Source: Organic Letters

DOI: 10.1021/acs.orglett.4c03242

Authors: Jordi Duran, Paula Rodríguez, Ward Vermeer, Xavier Companyó

Institution: Universitat de Barcelona

Language: English

Topic: Asymmetric Synthesis and Catalysis

Subfield: Organic Chemistry

Field: Chemistry

Domain: Physical Sciences

Open Access status: hybrid

Estimated APC paid: $4,500

Funders: Ministerio de Ciencia, Innovación y Universidades, Generalitat de Catalunya, Agència de Gestió d'Ajuts Universitaris i de Recerca