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使用钌催化剂将生物质衍生的乙酰丙酸室温不对称转移氢化制备光学纯γ-戊内酯

Room-Temperature Asymmetric Transfer Hydrogenation of Biomass-Derived Levulinic Acid to Optically Pure γ-Valerolactone Using a Ruthenium Catalyst.

作者信息

Shende Vaishali S, Raut Amol B, Raghav Prathamesh, Kelkar Ashutosh A, Bhanage Bhalchandra M

机构信息

Department of Chemistry, Institute of Chemical Technology, Mumbai 400019, India.

Chemical Engineering and Process Development Division, CSIR-National Chemical Laboratory, Pune 411008, India.

出版信息

ACS Omega. 2019 Nov 5;4(21):19491-19498. doi: 10.1021/acsomega.9b03424. eCollection 2019 Nov 19.

DOI:10.1021/acsomega.9b03424
PMID:31763574
原文链接:https://pmc.ncbi.nlm.nih.gov/articles/PMC6868911/
Abstract

This study presents a first report on ruthenium-catalyzed asymmetric transfer hydrogenation (ATH) of levulinic acid (LA) to chiral γ-valerolactone (GVL). ATH of LA has been explored with Noyori's chiral catalyst (Ru-TsDPEN) in methanol solvent. Efficacy of ATH reaction of LA was investigated under different reactions conditions such as temperature, catalyst, and hydrogen donor concentration. The effect of various organic tertiary bases along with formic acid (FA) as a hydrogen donor was studied, and -methylpiperidine with FA (1:1 molar ratio) was revealed as an efficient hydrogen donor for ATH of LA to GVL furnishing chiral GVL with complete conversion and 93% enantiomeric excess (ee). This operationally simple and mild ATH protocol was tested for practical applicability of ATH of LA obtained from biomass waste (rice husk and wheat straw) and furnished chiral GVL with 82% ee.

摘要

本研究首次报道了钌催化乙酰丙酸（LA）不对称转移氢化（ATH）制备手性γ-戊内酯（GVL）。在甲醇溶剂中，使用野依良治的手性催化剂（Ru-TsDPEN）对LA的ATH反应进行了探索。在不同反应条件下，如温度、催化剂和氢供体浓度，研究了LA的ATH反应效果。研究了各种有机叔碱以及作为氢供体的甲酸（FA）的影响，结果表明，-甲基哌啶与FA（摩尔比1:1）是将LA ATH制备GVL的有效氢供体，能使手性GVL完全转化，对映体过量（ee）达93%。该操作简单且温和的ATH方法用于从生物质废料（稻壳和麦秸）中获得的LA的ATH实际应用测试时，能得到ee为82%的手性GVL。

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