This report reviews the most important lipase-catalyzed strategies for the preparation
of pharmaceutically and chemically important tetrahydroisoquinoline and tetrahydro-β-carboline
enantiomers through O-acylation of the primary hydroxy group, N-acylation of the secondary
amino group, and COOEt hydrolysis of the corresponding racemic compounds with simple
molecular structure, which have been reported during the last decade. A brief introduction
describes the importance and synthesis of tetrahydroisoquinoline and tetrahydro-β-carboline
derivatives, and it formulates the objectives of this compilation. The strategies
are presented in chronological order, classified according to function of the reaction
type, as kinetic and dynamic kinetic resolutions, in the main text. These reactions
result in the desired products with excellent ee values. The pharmacological importance
of the products together with their synthesis is given in the main text. The enzymatic
hydrolysis of the hydrochloride salts as racemates of the starting amino carboxylic
esters furnished the desired enantiomeric amino carboxylic acids quantitatively. The
enzymatic reactions, performed in tBuOMe or H2O as usable solvents, and the transformations
carried out in a continuous-flow system, indicate clear advantages, including atom
economy, reproducibility, safer solvents, short reaction time, rapid heating and compression
vs. shaker reactions. These features are highlighted in the main text.
