Lewis Acid-Promoted Enantioselective Dearomative Spirocyclizations of Allenes.
J Org Chem
; 83(19): 12207-12212, 2018 10 05.
Article
en En
| MEDLINE
| ID: mdl-30141933
ABSTRACT
A chiral oxazaborolidine combined with SnCl4 has been found to promote the dearomative spirocyclization of electron-rich benzyl allenyl ketones. The reaction outcome is sensitive to the nature of activating acid, which was rationalized using hard-soft acid-base (HSAB) theory. The spirocyclic product was obtained with up to 72% ee, which is the best result reported to date for these substrates. The formation of cross-conjugated or conjugated products is readily controlled by changing the oxygen-protecting groups.
Texto completo:
1
Banco de datos:
MEDLINE
Asunto principal:
Compuestos de Espiro
/
Alquenos
/
Ácidos de Lewis
Idioma:
En
Año:
2018
Tipo del documento:
Article