Open AccessLipase-Mediated Dynamic Kinetic Resolution of 1-Phenylethanol Using Niobium Salts as Racemization Agents
Author(s) -
Vanessa M. Higa,
Willian S. Rocha,
Mirela Inês de Sairre,
Álvaro T. Omori
Publication year - 2021
Publication title -
journal of the brazilian chemical society
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.337
H-Index - 70
eISSN - 1678-4790
pISSN - 0103-5053
DOI - 10.21577/0103-5053.20210086
Subject(s) - racemization , kinetic resolution , chemistry , lipase , enantiomer , niobium , toluene , candida antarctica , organic chemistry , hydrate , crystallization , catalysis , enzyme , enantioselective synthesis
In this work, a racemization method of (S)-1-phenylethanol by niobium salts was developed. Among the salts available, the niobium phosphate hydrate (NbOPO4.nH2O) reduced the enantiomeric excess (ee) of the chiral alcohol from 95 to 0% after 24 h at 60 ºC in toluene. This new racemization agent was combined with a lipase (CALB) in order to achieve a chemoenzymatic dynamic kinetic resolution (DKR). Experiments demonstrated that the DKR process is feasible and the corresponding (R)-1-phenylethyl acetate was obtained with 92% conversion and 85% ee.