Chiral 2-alkylbranched acids, esters and alcohols. Preparation and stereospecific flavour evaluation

Article abstract of DOI:10.1016/S0957-4166(00)86137-6

Racemic 2-alkylbranched acids are transformed to diastereomeric derivatives with (S)-2-hydroxy-3-phenylpropionic acid-N-methylamide of (S)-(-)-1-phenylethylamine and separated by liquid chromatography to pure diastereoisomers, which are subsequently hydrolyzed to yield optically pure acids. Enantiomeric alcohols are generated by LiAlH₄-reduction of the corresponding acids, esters are synthesized by different methods. The odour impression of the enantiomeric compounds is investigated.