The generality of our new convenient synthesis of isopinocampheylamines by hydroboration-amination of α-pinene has been established by converting representative terpenes into optically pure terpenylamines, such as (-)-cis-caran-trans-2-amine, (-)-cis-caran-trans-4-amine, (-)-longifolamine, and (+)-cis-myrtanylamine. The synthesis involves converting the terpene into the B-chloroditerpenylborane by treatment with chloroborane-methyl sulfide. This is treated with trimethylaluminum to form the B-methylditerpenylborane, and the latter is converted into the amine by treatment with hydloxylamine-O-sulfonic acid. cis-Myrtanylamine has been shown to be as effective as isopinocampheylamine for the gas chromatographic analysis of racemic carboxylic acids as their diastereomeric amides, suggesting the generality of this application of terpenylamines as chiral derivatizing agents.
ASJC Scopus subject areas
- Physical and Theoretical Chemistry
- Organic Chemistry
- Inorganic Chemistry