Stereoselective Domino Rearrangement peri-Annulation of Cinchona Alkaloid Derivatives with 8-Bromo-1-naphthyl Grignard.
J Org Chem
; 87(17): 11602-11607, 2022 09 02.
Article
in En
| MEDLINE
| ID: mdl-35998654
ABSTRACT
The unexpected domino coupling and rearrangement of the Cinchona alkaloid skeleton has been found to occur in the reaction of 9-chloro-9-deoxy-alkaloids with Grignards from peri-dihalogenonaphthalene. The cyclization and migration of the central quinuclidinylmethyl group (C9) from position C-4' to position C-3' of quinoline formed a novel chiral ring system of 5-aza-7H-benzo[no]tetraphene, yielding products of unlike configuration. The proposed reaction pathway involves radical intermediates.
Full text:
1
Collection:
01-internacional
Database:
MEDLINE
Main subject:
Cinchona Alkaloids
/
Alkaloids
Language:
En
Journal:
J Org Chem
Year:
2022
Document type:
Article
Affiliation country:
Poland