Asymmetric Catalysis via Cyclic, Aliphatic Oxocarbenium Ions.
J Am Chem Soc
; 139(6): 2156-2159, 2017 02 15.
Article
em En
| MEDLINE
| ID: mdl-28169541
ABSTRACT
A direct enantioselective synthesis of substituted oxygen heterocycles from lactol acetates and enolsilanes has been realized using a highly reactive and confined imidodiphosphorimidate (IDPi) catalyst. Various chiral oxygen heterocycles, including tetrahydrofurans, tetrahydropyrans, oxepanes, chromans, and dihydrobenzofurans, were obtained in excellent enantioselectivities by reacting the corresponding lactol acetates with diverse enol silanes. Mechanistic studies suggest the reaction to proceed via a nonstabilized, aliphatic, cyclic oxocarbenium ion intermediate paired with the confined chiral counteranion.
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Base de dados:
MEDLINE
Idioma:
En
Revista:
J Am Chem Soc
Ano de publicação:
2017
Tipo de documento:
Article
País de afiliação:
Alemanha