Diversified Synthesis of Chiral Fluorinated Cyclobutane Derivatives Enabled by Regio- and Enantioselective Hydroboration.
Angew Chem Int Ed Engl
; 63(23): e202401451, 2024 Jun 03.
Article
de En
| MEDLINE
| ID: mdl-38563752
ABSTRACT
The diversified synthesis of chiral fluorinated cyclobutane derivatives has remained a difficult task in synthetic chemistry. Herein, we present an approach for asymmetric hydroboration and formal hydrodefluorination of gem-difluorinated cyclobutenes through rhodium catalysis, providing chiral gem-difluorinated α-boryl cyclobutanes and monofluorinated cyclobutenes with excellent regio- and enantioselectivity, respectively. The key to the success of the two transformations relies on an efficient, mild and highly selective rhodium-catalyzed asymmetric hydroboration with HBPin (pinacolborane), in which the subsequent addition of a base, and a catalytic amount of palladium in some cases, results in the formation of formal hydrodefluorination products with the four-membered ring retained. The obtained chiral gem-difluorinated α-boryl cyclobutanes are versatile building blocks that provide a platform for the synthesis of enantioenriched fluorinated cyclobutane derivatives to a great diversity.
Texte intégral:
1
Collection:
01-internacional
Base de données:
MEDLINE
Langue:
En
Journal:
Angew Chem Int Ed Engl
Année:
2024
Type de document:
Article
Pays d'affiliation:
Chine
Pays de publication:
Allemagne