Organoboranes for Synthesis. 16. A Convenient Synthesis of Enantiomerically Pure Isopinocampheylamine, a Chiral Derivatizing Agent for Gas Chromatographic Analysis of Optically Active Carboxylic Acids

Both isomers of enantiomerically pure isopinocampheylamine (1) have been synthesized from the corresponding B-chlorodiisopinocampheylborane by treatment with either methylmagnesium bromide or trimethylaluminum to form B-methyldiisopinocampheylborane, followed by treatment of the intermediate with hydroxylamine-O-sulfonic acid. Application of 1 as a derivatizing agent for the gas chromatographic analysis of optically active carboxylic acids has been demonstrated.