Organocatalytic Enantioselective Cycloetherifications Using a Cooperative Cation-Binding Catalyst.
Org Lett
; 20(17): 5319-5322, 2018 09 07.
Article
in En
| MEDLINE
| ID: mdl-30106303
ABSTRACT
A highly enantioselective cycloetherification strategy for the straightforward synthesis of enantioenriched tetrahydrofurans, tetrahydropyrans, and oxepanes using Song's cation-binding oligoEG catalyst and KF as the base is demonstrated. A wide range of ε-, ζ-, and η-hydroxy-α,ß-unsaturated ketones were cyclized to the corresponding five-, six-, and seven-membered chiral oxacycles with high enantiopurity. This remarkably successful catalysis can be ascribed to systematic cooperative cation-binding catalysis in a densely confined supramolecular chiral cage generated in situ from the chiral catalyst, substrate, and KF.
Full text:
1
Collection:
01-internacional
Database:
MEDLINE
Language:
En
Journal:
Org Lett
Journal subject:
BIOQUIMICA
Year:
2018
Document type:
Article