Regioselectivity switch based on the stoichiometry: stereoselective synthesis of trisubstituted vinyl epoxides by Cu-catalyzed 3-exo-trig cyclization of α-allenols

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/sulfony...

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Detalhes bibliográficos
Autores: Luna Costales, Amparo, Esteban Arderíus, Pablo, Herrera García, Fernando, San Martín Loubet, Daniel, Almendros Requena, Pedro
Tipo de documento: artigo
Data de publicação:2022
País:España
Recursos:Universidad Complutense de Madrid (UCM)
Repositório:Docta Complutense
Idioma:inglês
OAI Identifier:oai:docta.ucm.es:20.500.14352/114881
Acesso em linha:https://hdl.handle.net/20.500.14352/114881
Access Level:Acceso aberto
Palavra-chave:547
Allenes
Copper
Cyclization
Regioselectivity
Sulfones
Química orgánica (Química)
2306 Química Orgánica
2306.14 Química de Los Organosulfurados
Descrição
Resumo: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.

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