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Enantioselective Synthesis of Alkyl-Branched Alkanes. Synthesis of the Stereoisomers of 7,11-Dimethylheptadecane and 7-Methylheptadecane, Components of the Pheromone of Lambdina Species

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journal contribution
posted on 2000-10-06, 00:00 authored by David D. Díaz, Víctor S. Martín
The stereoisomers of 7,11-dimethylheptadecane and 7-methylheptadecane have been synthesized. The key step used has been the intramolecular hydride transfer from a secondary γ-benzyloxy group with defined absolute stereochemistry to a cation generated by Lewis acid treatment of the suitable tertiary Co2(CO)6-complexed propargylic alcohol. The application of this method provided stereochemically defined α-alkyl-γ-hydroxy-acetylenes that after hydrogenation and further reductive elimination of the hydroxyl group yielded sec-alkyl hydrocarbons.