Enantiospecific access to various C(9),C(10)-disubstituted camphors: scope and limitations.
The valuable chiral sources C(9),C(10)-disubstituted camphors can be enantiospecifically obtained from the corresponding C(9)-substituted camphors by a general and straightforward synthetic method. This method involves the electrophilic treatment of a key 2-methylenenorbornan-1-ol intermediate, followed by a controlled tandem carbon-carbon double-bond addition-Wagner-Meerwein rearrangement of the norbornane framework. Discussion of the results presented suggests possible extensions and limitations of the methodology used. The feasibility of this method has been exemplified by the highly efficient enantiospecific preparation of several interesting C(9)-halogen-, C(10)-halogen, O-, S-, or Se-substituted camphors.
Departamento de Química Orgánica I, Facultad de Ciencias Químicas, Universidad Complutense de Madrid, Ciudad Universitaria, 28040-Madrid, Spain.
Antonio García
AG
Martínez
Enrique Teso
ET
Vilar
Amelia García
AG
Fraile
Santiago
S
de la Moya Cerero
Cristina Díaz
CD
Morillo
Rocío Pérez
RP
Morillo
D002164:Camphor / Q000031:analogs & derivatives / Q000138:chemical synthesis*; D008968:Molecular Conformation; D013237:Stereoisomerism
D002164:Camphor