Synthetic Process Development of (R)-(+)-1,2-Epoxy-5-hexene: An Important Chiral Building Block

IF 3.1 3区化学 Q2 CHEMISTRY, APPLIED Organic Process Research & Development Pub Date : 2024-08-01 DOI:10.1021/acs.oprd.4c00101

Daryl Guthrie, John M. Saathoff, Rajkumar Lalji Sahani, Aline Nunes De Souza, Daniel W. Cook, Samuel R. Hochstetler, Justina M. Burns, Roudabeh Sadat Moazeni-Pourasil, Janie Wierzbicki, Saeed Ahmad, G. Michael Laidlaw, B. Frank Gupton, Charles S. Shanahan, Douglas A. Klumpp, Limei Jin

引用次数: 0

Abstract

Herein, we describe two practical approaches to synthesize (R)-(+)-1,2-epoxy-5-hexene from inexpensive and readily available raw materials and reagents. The first approach is a two-step sequence, involving an epoxidation with meta-chloroperoxybenzoic acid (mCPBA) and a chiral resolution with (salen)Co(II), producing (R)-(+)-1,2-epoxy-5-hexene in 24–30% overall yield. The second approach utilizes readily available (R)-epichlorohydrin as the starting material and features an epoxide ring-opening reaction with allylMgCl and the NaOH-mediated ring closure reaction. Development of this two-step process affords R-(+)-1,2-epoxy-5-hexene in overall isolated yields of 55–60% with an exceptional purity profile. Both approaches have been successfully demonstrated on 100–200 g scales.

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(R)-(+)-1,2-环氧-5-己烯的合成工艺开发：重要的手性结构单元

在此，我们介绍了利用廉价易得的原材料和试剂合成 (R)-(+)-1,2-环氧-5-己烯的两种实用方法。第一种方法分两步进行，包括用偏氯过氧苯甲酸（mCPBA）进行环氧化反应和用（salen）Co(II)进行手性解析，以 24-30% 的总收率生成 (R)-(+)-1,2-环氧-5-己烯。第二种方法利用现成的(R)-环氧氯丙烷作为起始原料，并与烯丙基氯化镁发生环氧化物开环反应，以及由 NaOH 介导的闭环反应。开发这种两步法生产 R-(+)-1,2-环氧-5-己烯，总分离产率为 55-60%，纯度极高。这两种方法都已在 100-200 克的规模上成功验证。

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

Organic Process Research & Development 化学-应用化学

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.