Author, as appears in the article.: Pujol, M; Méndez, M; Fernández, E

Department: Química Física i Inorgànica

URV's Author/s: Fernández Gutiérrez, Maria Elena / Pujol Martí, Mireia

Keywords: Substitution Stereocontrolled approach Esters Electrophilic cyclization Alpha-pyrones Alkynes Alkenes 1,1-diborylalkenes

Abstract: The key to a successful C-B activation is to discriminate between two geminal boryl moieties that are exposed to the same reaction conditions. Here we describe a stereoselective C-B activation of beta,beta-diboryl acrylates forming exclusively the (Z)-alpha-borylalkenyl copper(I) key intermediate, for subsequent allylic alkylation reactions. The new borylated (Z)-skipped dienoates followed a feasible iodo-lactonization sequence for the preparation of borylated lactone cores, which can be used in drug discovery.

Thematic Areas: Química Physical and theoretical chemistry Organic chemistry Medicina ii Medicina i Materiais Interdisciplinar General medicine Farmacia Ciências biológicas ii Ciências biológicas i Ciências agrárias i Chemistry, organic Biotecnología Biodiversidade Biochemistry

licence for use: https://creativecommons.org/licenses/by/3.0/es/

Author's mail: mireia.pujol@urv.cat mariaelena.fernandez@urv.cat

Author identifier: 0000-0001-9025-1791

Record's date: 2024-02-24

Papper version: info:eu-repo/semantics/publishedVersion

Link to the original source: https://pubs.acs.org/doi/full/10.1021/acs.orglett.3c03640

Papper original source: Organic Letters.

APA: Pujol, M; Méndez, M; Fernández, E (2023). Stereoselective Control of the Cu Activation of β,β-Diboryl Acrylates for Allylic Coupling Protocols with Concomitant Lactonization. Organic Letters, (), -. DOI: 10.1021/acs.orglett.3c03640

Licence document URL: http://repositori.urv.cat/ca/proteccio-de-dades/

Article's DOI: 10.1021/acs.orglett.3c03640

Entity: Universitat Rovira i Virgili

Journal publication year: 2023

Publication Type: Journal Publications