Practical access to (S)-heterocyclic aromatic acetates via CAL-B/Na2CO3-deacylation and Mitsunobu reaction protocol

IF 1.4 4区生物学 Q4 BIOCHEMISTRY & MOLECULAR BIOLOGY

Biocatalysis and Biotransformation Pub Date : 2022-01-31 DOI:10.1080/10242422.2022.2030726

Louisa Aribi‐Zouioueche, Mounia Merabet-Khelassi, Nabila Braïa, M. Toffano

引用次数: 1

Abstract

Abstract Herein, we report the preparation of enantiomerically pure forms of 2,3-dihydrobenzofuran-3-ol (1), chroman-4-ol (2), thiochroman-4-ol (3), 1-(furan-2-yl) ethanol (5) and 1-(thiophen-2-yl) ethanol (6), through a kinetic resolution catalysed by Candida antarctica lipase B/Na2CO3 hydrolysis sequence in organic media. The (R)-furnished alcohols and the (S)-remained acetates are recovered enantiopures (ee >99%, E ≫ 200, Conv = 50%). Those ideal enzymatic kinetic resolution (EKRs) are well incorporated to the Mitsunobu inversion protocol in a one pot procedure to give (S)-heterocyclic acetates (1a–3a) in good to high enantiomeric excess (88%–92% ee). Whilst, the (S)-heteroaromatic acetates (5a and 6a) are given with moderate enantiomeric excess (51%–62% ee). All the (S)-acetates are given in good isolated chemical yields (>80%) allowing to overcome the maximum of 50% yield which could be usually reached in a regular kinetic resolution processes. Graphical Abstract

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通过CAL-B/Na2CO3脱酰和Mitsunobu反应方案实际获得（S）-杂环芳族乙酸酯

摘要本文报道了在有机介质中，通过南极念珠菌脂肪酶B/Na2CO3水解序列催化的动力学拆分，制备对映体纯形式的2，3-二氢苯并呋喃-3-醇（1）、色满-4-醇（2）、硫色满4-醇（3）、1-（呋喃-2-基）乙醇（5）和1-（噻吩-2-基）醇（6）。（R）提供的醇和（S）保留的乙酸盐被回收对映体（ee＞99%，E＜200，Conv＝50%）。这些理想的酶动力学拆分（EKRs）在一锅法中很好地结合到Mitsunobu转化方案中，得到对映体过量（88%–92%ee）的（S）-杂环乙酸酯（1a–3a）。同时，（S）-杂芳族乙酸酯（5a和6a）具有适度的对映体过量（51%-62%ee）。所有（S）-醋酸盐都以良好的分离化学产率（>80%）提供，从而克服了通常在常规动力学拆分过程中可以达到的50%的最大产率。图形摘要

本文章由计算机程序翻译，如有差异，请以英文原文为准。

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来源期刊

Biocatalysis and Biotransformation 生物-生化与分子生物学

CiteScore

4.40

自引率

5.60%

发文量

审稿时长

3 months

期刊介绍： Biocatalysis and Biotransformation publishes high quality research on the application of biological catalysts for the synthesis, interconversion or degradation of chemical species. Papers are published in the areas of: Mechanistic principles Kinetics and thermodynamics of biocatalytic processes Chemical or genetic modification of biocatalysts Developments in biocatalyst''s immobilization Activity and stability of biocatalysts in non-aqueous and multi-phasic environments, including the design of large scale biocatalytic processes Biomimetic systems Environmental applications of biocatalysis Metabolic engineering Types of articles published are; full-length original research articles, reviews, short communications on the application of biotransformations, and preliminary reports of novel catalytic activities.