The enantiomers of 1,2,3,4-tetrahydroisoquinoline- and 6,7-dimethoxy-1,2,3,4-tetrahydroisoquinoline-1-acetic acids were prepared via Burkholderia cepacia lipase (lipase PS-D)-catalyzed kinetic resolution of the corresponding ethyl and 2-methoxyethyl esters using enantioselective (E > 200) hydrolysis in DIPE. The (S)-acids were produced enzymatically, whereas the (R)-acids were obtained via the chemical hydrolysis of the unreacted (R)-esters. The solvent and its water content had major effects on both reactivity and enantioselectivity. The methoxyethyl moiety of the ester had a key role concerning the reactivity of the substrates.
ASJC Scopus subject areas
- Physical and Theoretical Chemistry
- Organic Chemistry
- Inorganic Chemistry