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 CO
OEt hydrolysis of the
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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 CO
OEt 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 H
2O 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.
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