Oxidatively Initiated NHC-Catalyzed Enantioselective Synthesis of 3,4-Disubstituted Cyclopentanones from Enals.
J Am Chem Soc
; 137(32): 10112-5, 2015 Aug 19.
Article
em En
| MEDLINE
| ID: mdl-26256839
ABSTRACT
An unprecedented N-heterocyclic carbene (NHC)-catalyzed annulation of enals to form 3,4-disubstituted cyclopentanones has been discovered. Aryl enals undergo dimerization in the presence of a single-electron oxidant to form C2 symmetric cyclopentanones. A cross-reaction has also been developed, allowing for the synthesis of differentially substituted cyclopentanones. Mechanistically, the reaction is thought to proceed through radical intermediates, further establishing the synthetic utility of this class of reactivity.
Texto completo:
1
Base de dados:
MEDLINE
Assunto principal:
Ciclopentanos
/
Técnicas de Química Sintética
Idioma:
En
Ano de publicação:
2015
Tipo de documento:
Article