连续流对映体选择性合成：聚合物支持的异硫脲催化与 α-偶氮-2-基苯乙酮的对映体选择性迈克尔加成-环化反应

IF 3.1 3区化学 Q2 CHEMISTRY, APPLIED Organic Process Research & Development Pub Date : 2024-05-02 DOI:10.1021/acs.oprd.4c00113

Zhanyu Zhou, Kevin Kasten, Tengfei Kang, David B. Cordes and Andrew D. Smith*,

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引用次数: 0

摘要

一种含有聚合物支撑的异硫脲 HyperBTM 催化剂衍生物的填料反应床已被用于促进一系列杂环产品的对映体选择性合成，这些产品来源于α-偶氮唑-2-基苯乙酮和-乙酰胺与烷基、芳基和杂环α,β-不饱和均酸酐通过α,β-不饱和酰基铵中间体在连续流中的结合。生成的产品收率高至极好，对映体纯度通常也非常高（高达 97:3）。在 15 毫摩尔的规模上进行了放大，重结晶后杂环产物的总收率为 68%，对映体纯度为 98:2。

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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Enantioselective Synthesis in Continuous Flow: Polymer-Supported Isothiourea-Catalyzed Enantioselective Michael Addition–Cyclization with α-Azol-2-ylacetophenones

A packed reactor bed incorporating a polymer-supported isothiourea HyperBTM catalyst derivative has been used to promote the enantioselective synthesis of a range of heterocyclic products derived from α-azol-2-ylacetophenones and -acetamides combined with alkyl, aryl, and heterocyclic α,β-unsaturated homoanhydrides in continuous flow via an α,β-unsaturated acyl-ammonium intermediate. The products are generated in good to excellent yields and generally in excellent enantiopurity (up to 97:3 er). Scale-up is demonstrated on a 15 mmol scale, giving the heterocyclic product in 68% overall yield with 98:2 er after recrystallization.

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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.