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1990•Zeitschrift für Naturforschung BOpen access

Optical Resolution of Racemic Jasmonic Acid by Separation of Diastereomeric Mandelyl Esters

Robert Kramell, Gernot Schneider, Jurgen G. Schmidt, Günther Sembdner, Klaus Schréiber

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Abstract

The reaction of racemic jasmonic acid with either (R)-mandelic acid or its (S)-enantiomer resulted in a mixture of diastereomeric esters. Both the O-[(±)-jasmonoyl]-(R)-mandelic acids (2a, 2b) and the O-[(±)-jasmonoyl]-(S)-mandelic acids (3a, 3b) could be separated by silica gel chromatography. By hydrolysis of the pure diastereomers, resolved (+)-JA (la) and (–)-JA (lb) were obtained. The structures and the purity of all compounds were confirmed by 1H NMR, MS, GC/MS, IR and ORD.

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The reaction of racemic jasmonic acid with either (R)-mandelic acid or its (S)-enantiomer resulted in a mixture of diastereomeric esters. Both the O-[(±)-jasmonoyl]-(R)-mandelic acids (2a, 2b) and the O-[(±)-jasmonoyl]-(S)-mandelic acids (3a, 3b) could be separated by silica gel chromatography. By hydrolysis of the pure diastereomers, resolved (+)-JA (la) and (–)-JA (lb) were obtained. The structures and the purity of all compounds were confirmed by 1H NMR, MS, GC/MS, IR and ORD.

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Available abstract

The reaction of racemic jasmonic acid with either (R)-mandelic acid or its (S)-enantiomer resulted in a mixture of diastereomeric esters. Both the O-[(±)-jasmonoyl]-(R)-mandelic acids (2a, 2b) and the O-[(±)-jasmonoyl]-(S)-mandelic acids (3a, 3b) could be separated by silica gel chromatography. By hydrolysis of the pure diastereomers, resolved (+)-JA (la) and (–)-JA (lb) were obtained. The structures and the purity of all compounds were confirmed by 1H NMR, MS, GC/MS, IR and ORD.

Key concepts: Diastereomer, Mandelic acid, Chemistry, Enantiomer, Hydrolysis, Organic chemistry, Enantiomeric excess, Resolution (logic)

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