Asymmetric reduction of aromatic heterocyclic ketones with bio-based catalyst Lactobacillus kefiri P2
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ORIGINAL PAPER
Asymmetric reduction of aromatic heterocyclic ketones with bio‑based catalyst Lactobacillus kefiri P2 Yasemin Baydaş1 · Erbay Kalay2 · Engin Şahin3 Received: 9 July 2020 / Accepted: 15 September 2020 © Institute of Chemistry, Slovak Academy of Sciences 2020
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-(benzofuran2-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-(benzofuran2-yl)ethanol
Introduction Electronic supplementary material The online version of this article (https://doi.org/10.1007/s11696-020-01364-2) contains supplementary material, which is available to authorized users. * Engin Şahin [email protected] Extended author information available on the last page of the article
Chirality has become important in various industries such as, pharmaceutical, agrochemical and fine chemical. Chiral aromatic and hetero aromatic alcohols are widely used for synthetic procedures in the pharmaceutical and finechemical industries, owing to their stable structure (Quaglia et al. 2013). The functional groups of chiral secondary alcohols can be easily transformed into other functional
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groups without racemation (Şahin and Dertli 2019). Enantiopure 1-phenylethanol and its derivatives are useful chiral building blocks or intermediates for synthesis of various complex molecules used in a spectrum of industries. For instance, (S)-1-phenyl ethanol, 2-naphthyl ethanol and (S)1-(3-methoxyphenyl) ethanol are used as chiral auxiliaries in chemical and pharmaceutical industries (Lou et al. 2009; Mangas-Sánchez et al. 2009). On the other hand, important examples of heteroarylmethanols are (R)-neobenodi
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