Author, as appears in the article.: Hurtado, Josebe; Iragorri, Nerea; Reyes, Efraim; Vicario, Jose L; Fernandez, Elena
Department: Química Física i Inorgànica
URV's Author/s: Fernández Gutiérrez, Maria Elena / Fernández López, Elena
Keywords: Alcohols Asymmetric allylic substitution Axial-to-point chirality Axial-to-point chirality * diastereoconvergence * desymmetrization * copper catalysis * homoallylic alcohols Carbonates Complexes Copper catalysis Desig Desymmetrization Diastereoconvergence Diboron Efficient route Homoallylic alcohol Homoallylic alcohols Olefination Tertiary Wittig reaction
Abstract: Cu-catalyzed asymmetric allylic borylation of 3,3'-disubstituted 1-vinylcyclobutan-1-ols renders axially chiral allylborane systems, with high asymmetric induction for both enantiomers, by precise selection of the cis or trans substrate. The enantioenriched alkylidenecyclobutanes served as chiral platform to prove the conceptually challenging transference of the axial-to-point chirality through two new stereocenters and one pseudoasymmetric carbon generated via diastereoconvergent allylation of aldehydes, without enantioselective erosion. Desymmetrization of 1-vinylcyclobutanols via asymmetric Cu-catalyzed borylation creates axially chiral allylboranes in high enantiomeric ratio for both enantiomers. The axial-to-chiral transfer is possible through diastereoconvergent allylation with aldehydes, proving the preference for the same diastereoisomeric homoallylic alcohol, creating two new stereocenters and one pseudoasymemtric center with stereoretention for both enantiomers. image
Thematic Areas: Astronomia / física Catalysis Chemistry Chemistry (all) Chemistry (miscellaneous) Chemistry, multidisciplinary Ciências biológicas i Ciências biológicas ii Ciências biológicas iii Engenharias ii Farmacia General chemistry General medicine Interdisciplinar Materiais Medicina i Medicina ii Química
licence for use: https://creativecommons.org/licenses/by/3.0/es/
Author's mail: mariaelena.fernandez@urv.cat
Author identifier: 0000-0001-9025-1791
Record's date: 2024-11-09
Papper version: info:eu-repo/semantics/publishedVersion
Papper original source: Angewandte Chemie (International Ed. Print). 63 (43): e202411232-
APA: Hurtado, Josebe; Iragorri, Nerea; Reyes, Efraim; Vicario, Jose L; Fernandez, Elena (2024). Cu-Catalyzed Enantioselective Borylative Desymmetrization of 1-Vinyl Cyclobutanols and Axial-to-Point Chirality Transfer in a Diastereoconvergent/Stereoretentive Allylation Scenery. Angewandte Chemie (International Ed. Print), 63(43), e202411232-. DOI: 10.1002/anie.202411232
Licence document URL: https://repositori.urv.cat/ca/proteccio-de-dades/
Entity: Universitat Rovira i Virgili
Journal publication year: 2024
Publication Type: Journal Publications
Repositori URV