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Published on: February 7, 2019
Enantiospecific access to various C(9),C(10)-disubstituted camphors: scope and limitations
Antonio García Martínez1, Enrique Teso Vilar, Amelia García Fraile
1Departamento de Química Orgánica I, Facultad de Ciencias Químicas, Universidad Complutense de Madrid, Ciudad Universitaria, 28040-Madrid, Spain.
Abstract:
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.
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