Enhancing the Asymmetric Hydrogenation/Desymmetrization of an Achiral Lactone in the Synthesis of (+)-Biotin

IF 3.1 3区 化学 Q2 CHEMISTRY, APPLIED Organic Process Research & Development Pub Date : 2025-02-06 DOI:10.1021/acs.oprd.4c00359
Werner Bonrath, Roman Goy, Achim Link, Felix Spindler, Jonathan A. Medlock, Marc-André Müller
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Abstract

(+)-Biotin plays an essential role as a cofactor in many biological systems and is used to supplement the diets of humans and animals. One of the most elegant chemical production processes involves the asymmetric hydrogenation/desymmetrization of a meso-anhydride to yield the key lactone intermediate. However, relatively high catalyst loadings limit the attractiveness of this route. A number of strategies have been investigated to improve the efficiency of the hydrogenation process, and an improved two-step process has been developed, which significantly reduces the amount of expensive chiral catalyst required and pairs this with a cheap, readily available nickel catalyst, producing the key chiral lactone without a reduction in the enantioselectivity.

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来源期刊
CiteScore
6.90
自引率
14.70%
发文量
251
审稿时长
2 months
期刊介绍: The journal Organic Process Research & Development serves as a communication tool between industrial chemists and chemists working in universities and research institutes. As such, it reports original work from the broad field of industrial process chemistry but also presents academic results that are relevant, or potentially relevant, to industrial applications. Process chemistry is the science that enables the safe, environmentally benign and ultimately economical manufacturing of organic compounds that are required in larger amounts to help address the needs of society. Consequently, the Journal encompasses every aspect of organic chemistry, including all aspects of catalysis, synthetic methodology development and synthetic strategy exploration, but also includes aspects from analytical and solid-state chemistry and chemical engineering, such as work-up tools,process safety, or flow-chemistry. The goal of development and optimization of chemical reactions and processes is their transfer to a larger scale; original work describing such studies and the actual implementation on scale is highly relevant to the journal. However, studies on new developments from either industry, research institutes or academia that have not yet been demonstrated on scale, but where an industrial utility can be expected and where the study has addressed important prerequisites for a scale-up and has given confidence into the reliability and practicality of the chemistry, also serve the mission of OPR&D as a communication tool between the different contributors to the field.
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