基于 [1,3]- 质子转移反应获得光学活性四氟乙烯胺。

IF 2.2 4区化学 Q2 CHEMISTRY, ORGANIC

Beilstein Journal of Organic Chemistry Pub Date : 2024-11-01 eCollection Date: 2024-01-01 DOI:10.3762/bjoc.20.233

Yuta Kabumoto, Eiichiro Yoshimoto, Bing Xiaohuan, Masato Morita, Motohiro Yasui, Shigeyuki Yamada, Tsutomu Konno

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引用次数: 0

摘要

室温至 50 °C，用 2.4 等量的 DBU 在甲苯中处理各种 (R)-N-(2,2,3,3-四氟戊-4-烯-1-亚基)-1-苯乙胺衍生物 24 小时，可顺利进行[1,3]-质子转移反应，且手性转移率高，从而以可接受的产率得到相应的重排产物。这些产物无需纯化，即可进行酸水解和随后的 N-Cbz 保护，从而以中等的三步收率得到具有光学活性的四氟乙烯酰胺。

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Access to optically active tetrafluoroethylenated amines based on [1,3]-proton shift reaction.

Treatment of various (R)-N-(2,2,3,3-tetrafluoropent-4-en-1-ylidene)-1-phenylethylamine derivatives with 2.4 equiv of DBU in toluene at room temperature to 50 °C for 24 h led to a smooth [1,3]-proton shift reaction with a high chirality transfer, affording the corresponding rearranged products in acceptable yields. Without purification, these products were subjected to acid hydrolysis and the subsequent N-Cbz protection, providing the optically active tetrafluoroethylenated amides in moderate three-step yields.

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来源期刊

Beilstein Journal of Organic Chemistry 化学-有机化学

CiteScore

4.90

自引率

3.70%

发文量

167

审稿时长

1.4 months

期刊介绍： The Beilstein Journal of Organic Chemistry is an international, peer-reviewed, Open Access journal. It provides a unique platform for rapid publication without any charges (free for author and reader) – Platinum Open Access. The content is freely accessible 365 days a year to any user worldwide. Articles are available online immediately upon publication and are publicly archived in all major repositories. In addition, it provides a platform for publishing thematic issues (theme-based collections of articles) on topical issues in organic chemistry. The journal publishes high quality research and reviews in all areas of organic chemistry, including organic synthesis, organic reactions, natural product chemistry, structural investigations, supramolecular chemistry and chemical biology.