Organoboranes for synthesis 17. Generality of Hydroboration-amination for the conversion of terpenes into enantiomerically pure terpenylamines. The utility for gas chromatographic analysis of chiral carboxylic acids

Herbert C. Brown, Sanjay V. Malhotra, P. Veeraraghavan Ramachandran

Research output: Contribution to journalArticlepeer-review

19 Scopus citations

Abstract

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.

Original languageEnglish (US)
Pages (from-to)3527-3534
Number of pages8
JournalTetrahedron Asymmetry
Volume7
Issue number12
DOIs
StatePublished - Dec 1996
Externally publishedYes

ASJC Scopus subject areas

  • Catalysis
  • Physical and Theoretical Chemistry
  • Organic Chemistry
  • Inorganic Chemistry

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