Three-Component Synthesis of Substituted Perhydropyrans from ß-Styrylmalonates, Aldehydes, and Alkoxyaluminum Dichlorides.
Org Lett
; 26(5): 1022-1027, 2024 Feb 09.
Article
de En
| MEDLINE
| ID: mdl-38284999
ABSTRACT
A three-component synthesis of substituted dimethyl dihydro-2H-pyran-3,3(4H)-dicarboxylates in up to 80% yields by the reaction of ß-styrylmalonates with aromatic or aliphatic aldehydes in the presence of ROAlCl2 prepared in advance either by exposure of EtAlCl2 with air access or by mixing equimolar amounts of AlCl3 with a primary or secondary alcohol has been developed. If EtAlCl2, itself, is used, dihydro-2H-pyran-3,3(4H)-diesters are not formed at all, while dimerization of styrylmalonates by (4 + 2)-annulation-type to give substituted tetrahydronaphthalenes is the main process. The possibility of using the CH-O-Al fragment of alkoxyaluminum dichlorides in cycloaddition reactions with α-CH-functionalization has been shown for the first time.
Texte intégral:
1
Collection:
01-internacional
Base de données:
MEDLINE
Langue:
En
Journal:
Org Lett
Sujet du journal:
BIOQUIMICA
Année:
2024
Type de document:
Article
Pays de publication:
États-Unis d'Amérique