2026-06-29T08:19:35Zhttps://docta.ucm.es/rest/oai/requestoai:docta.ucm.es:20.500.14352/1148812025-08-04T16:05:13Zcom_20.500.14352_14col_20.500.14352_15
Regioselectivity switch based on the stoichiometry: stereoselective synthesis of trisubstituted vinyl epoxides by Cu-catalyzed 3-exo-trig cyclization of α-allenols
Luna Costales, Amparo
Esteban Arderíus, Pablo
Herrera García, Fernando
San Martín Loubet, Daniel
Almendros Requena, Pedro
547
Allenes
Copper
Cyclization
Regioselectivity
Sulfones
Química orgánica (Química)
2306 Química Orgánica
2306.14 Química de Los Organosulfurados
Typical transition metal-catalyzed oxycyclization of allenols takes place at the terminal allene carbon via a 5-endo path and forms dihydrofurans. A copper-catalyzed protocol brought about a reversed regioselectivity, generating a series of trisubstituted epoxides through a 3-exo-cyclization/sulfonylation cascade. The current stoichiometry control of regioselectivity may open singular opportunities in chemical transformations.
Ministerio de Ciencia e Innovación (España)
European Commission
Depto. de Química Orgánica
Fac. de Ciencias Químicas
TRUE
pub
2025-01-17T11:18:36Z
2025-01-17T11:18:36Z
2022
journal article
AM
https://hdl.handle.net/20.500.14352/114881
1615-4150
10.1002/adsc.202200592
1615-4169
eng
MCIN/AEI /10.13039/501100011033
info:eu-repo/grantAgreement/AEI/Plan Estatal de Investigación Científica y Técnica y de Innovación 2017-2020/PGC2018-095025-B-I00/ES/NUEVAS ESTRATEGIAS SINTETICAS DE CICLACION Y REAGRUPAMIENTO BASADAS EN ALENOS Y ALQUINOS PARA LA SINTESIS EFICIENTE DE MOLECULAS ORGANICAS DE INTERES/
Esteban P, Herrera F, San Martín D, Luna A, Almendros P. Regioselectivity Switch Based on the Stoichiometry: Stereoselective Synthesis of Trisubstituted Vinyl Epoxides by Cu‐Catalyzed 3‐exo‐trig Cyclization of α‐Allenols. Advanced Synthesis & Catalysis. 2022, 364, 3289–3294.
Attribution-NonCommercial-NoDerivatives 4.0 International
http://creativecommons.org/licenses/by-nc-nd/4.0/
open access
application/pdf
application/pdf
Wiley