Enantioselective enzymatic preparation of chiral glutaric monocarboxylic acids and amides

Enantioselective hydrolyses and ammonolyses of diethyl-3-hydroxyglutarate (1) and dimethyl-3-hydroxyglutarate (2) gave a maximum of 91 and 98% enantiomeric excess (ee), respectively, using immobilized lipase B from Candida antarctica. The ees were determined using chiral GLC of the monoamides and achiral GLC of diasteromeric derivatives of the monocarboxylic acids. The catalyst was re-used more than 10 times with retention of high activity and selectivity.