Enantioselective Tail-to-Head Cyclizations Catalyzed by Dual-Hydrogen-Bond Donors.
J Am Chem Soc
; 142(15): 6951-6956, 2020 04 15.
Article
em En
| MEDLINE
| ID: mdl-32223127
ABSTRACT
Chiral urea derivatives are shown to catalyze enantioselective tail-to-head cyclization reactions of neryl chloride analogues. Experimental data are consistent with a mechanism in which π-participation by the nucleophilic olefin facilitates chloride ionization and thereby circumvents simple elimination pathways. Kinetic and computational studies support a cooperative mode of catalysis wherein two molecules of the urea catalyst engage the substrate and induce enantioselectivity through selective transition state stabilization.
Texto completo:
1
Base de dados:
MEDLINE
Assunto principal:
Ligação de Hidrogênio
Limite:
Humans
Idioma:
En
Ano de publicação:
2020
Tipo de documento:
Article