Oxetan-3-ols as 1,2-bis-Electrophiles in a Brønsted-Acid-Catalyzed Synthesis of 1,4-Dioxanes.
Org Lett
; 24(12): 2365-2370, 2022 04 01.
Article
in En
| MEDLINE
| ID: mdl-35311271
Annulations that combine diacceptors with bis-nucleophiles are uncommon. Here, we report the synthesis of 1,4-dioxanes from 3-aryloxetan-3-ols, as 1,2-bis-electrophiles and 1,2-diols. Brønsted acid Tf2NH catalyzes both the selective activation of the oxetanol, to form an oxetane carbocation that reacts with the diol, and intramolecular ring opening of the oxetane. High regio- and diastereoselectivity are achieved with unsymmetrical diols. The substituted dioxanes and fused bicyclic products present interesting motifs for drug discovery and can be further functionalized.
Full text:
1
Collection:
01-internacional
Database:
MEDLINE
Main subject:
Dioxanes
/
Alcohols
Language:
En
Journal:
Org Lett
Journal subject:
BIOQUIMICA
Year:
2022
Document type:
Article
Country of publication:
United States