Optimisation, scope and advantages of the synthesis of chiral phenylethanols using whole seeds of Bauhinia variegata L. (Fabaceae) as a new and stereoselective bio-reducer of carbonyl compounds

DEMMEL, GABRIELA I.; BORDÓN, DANIELA L.; VÁZQUEZ, ANA M.; DECARLINI, MARÍA F.; RUIZ, GUSTAVO M.; CANTERO, JUAN J.; ROSSI, LAURA I.; AIMAR, MARIO L.

BIOCATALYSIS AND BIOTRANSFORMATION

TAYLOR & FRANCIS LTD

Año: 2021 vol. 39 p. 109 - 109

1024-2422

ith the aim of finding new methods for environmentally friendly synthesis of chiral phenylethanols, a screening was carried out to identify seeds that could be used as a biocatalyst capable of reducing stereoselectively prochiral ketones. As a result, seeds of Bauhinia variegata L. (Fabaceae) were identified as being an efficient and stereoselective biological reducer of acetophenoneto produce (S)-1-phenylethanol (conversion of 98% and 99 e.e.%). Then, to optimise the reductive process, the effects of some variables such as temperature, load of substrate, pH, co-solvent, and reuse and storability of the seeds as a function of time were established. Utilising the optimal reaction conditions, nineteen substituted acetophenones were reduced to their corresponding chiral alcohols with a conversion ranging from 30% to 98% and enantiomeric excess of between 65% and >99%, and in addition, useful key intermediates were also obtained by the synthesis of drugs. The scope and advantages of this