碳酸叔丁酯在环氧化合物开环中的亲核作用：5-（羟甲基）恶唑烷-2-酮的级联合成

IF 3.6 2区化学 Q1 CHEMISTRY, ORGANIC

Journal of Organic Chemistry Pub Date : 2025-06-04 DOI:10.1021/acs.joc.5c0053710.1021/acs.joc.5c00537

Kelly Lee, Xsingyi Lee, Ci-Yi Zhou, Yung-Lan Chu and Cheng-Kun Lin*,

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引用次数: 0

摘要

我们报道了在boc20介导的环氧化合物开环级联反应中，以碳酸叔丁基为亲核试剂高效、可扩展地合成了5-（羟甲基）恶唑烷-2-酮。优化发现Et3N是高收率的关键，其吸电子芳基进一步提高了效率（高达91%）。机理研究支持碳酸叔丁酯的亲核作用。这种通用的方法可以获得药学上相关的化合物，包括利奈唑胺的中间体，突出了其在药物化学中的价值。

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tert-Butyl Carbonate as a Nucleophile in Epoxide Ring Opening: A Cascade Synthesis of 5-(Hydroxymethyl)oxazolidin-2-one

We report an efficient and scalable synthesis of 5-(hydroxymethyl)oxazolidin-2-ones using tert-butyl carbonate as a nucleophile in a Boc₂O-mediated epoxide ring-opening cascade. Optimization identified Et₃N as key to high yields, with electron-withdrawing aryl groups further enhancing efficiency (up to 91%). Mechanistic studies support the nucleophilic role of tert-butyl carbonate. This versatile method enables access to pharmaceutically relevant compounds, including intermediates for Linezolid, highlighting its value in medicinal chemistry.

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来源期刊

Journal of Organic Chemistry 化学-有机化学

CiteScore

6.20

自引率

11.10%

发文量

1467

审稿时长

2 months

期刊介绍： Journal of Organic Chemistry welcomes original contributions of fundamental research in all branches of the theory and practice of organic chemistry. In selecting manuscripts for publication, the editors place emphasis on the quality and novelty of the work, as well as the breadth of interest to the organic chemistry community.