Synthesis of cis-Oriented Vicinal Diphenylethylenes through a Lewis Acid-Promoted Annulation of Oxotriphenylhexanoates.
J Org Chem
; 86(13): 8660-8671, 2021 07 02.
Article
in En
| MEDLINE
| ID: mdl-34138578
ABSTRACT
This study explores the synthesis of cyclic cis-vicinal phenyl ethylenes from oxotriphenylhexanoates. The reaction is a BBr3-promoted cyclization of 1,6-ketoesters (1) to five-membered diketo compounds (2). The synthesis is interesting as it constitutes one of the few examples of modular stereoselective synthesis of structures with a cis-oriented vicinal diphenylethylene. The core structure of 2 can be smoothly derivatized, which makes it a promising synthetic building block for further stereoselective synthetic applications.
Full text:
1
Collection:
01-internacional
Database:
MEDLINE
Main subject:
Ethylenes
/
Lewis Acids
Language:
En
Journal:
J Org Chem
Year:
2021
Document type:
Article
Affiliation country:
Sweden