ISSN print edition: 0366-6352 ISSN electronic edition: 1336-9075 Registr. No.: MK SR 9/7 Published monthly

Asymmetric reduction of aromatic heterocyclic ketones with bio-based catalyst Lactobacillus kefiri P2

Yasemin Baydaş, Erbay Kalay, and Engin Şahin

Department of Food Engineering, Faculty of Engineering, Bayburt University, Bayburt, Turkey

E-mail: esahin@bayburt.edu.tr

Received: 9 July 2020  Accepted: 15 September 2020

Abstract:

Abstract

Chiral heterocyclic secondary alcohols have received much attention due to their widespread use in pharmaceutical intermediates. In this study, Lactobacillus kefiri P2 biocatalysts isolated from traditional dairy products, were used to catalyze the asymmetric reduction of prochiral ketones to chiral secondary alcohols. Secondary chiral carbinols were obtained by asymmetric bioreduction of different prochiral substrates with results up to > 99% enantiomeric excess (ee). (R)-1-(benzofuran-2-yl)ethanol 5a, which can be used in the synthesis of pharmaceuticals such as bufuralols potent nonselective β-blockers antagonists, Amiodarone (cardiac anti-arrhythmic), and Benziodarone (coronary vasodilator), was produced in gram-scale, high yield and enantiomerically pure form using L. kefiri P2 biocatalysts. The gram-scale production was carried out, and 9.70 g of (R)-5a in enantiomerically pure form was obtained in 96% yield. Also, production of (R)-5a in terms of yield and gram scale through catalytic asymmetric reduction using the biocatalyst was the highest report so far. This is a cost-effective, clean and eco-friendly process for the preparation of chiral secondary alcohols compared to chemical processes. From an environmental and economic perspective, this biocatalytic method has great application potential, making it a green and sustainable way of synthesis.

Graphical Abstract

Keywords: Asymmetric reduction; Lactobacillus kefiri; Chiral alcohol; Biocatalytic transformation; (R)-1-(benzofuran-2-yl)ethanol

Full paper is available at www.springerlink.com.

DOI: 10.1007/s11696-020-01364-2

Chemical Papers 75 (3) 1147–1155 (2021)