Hypervalent iodine-mediated cyclization of bishomoallylamides to prolinols.

IF 2.2 4区 化学 Q2 CHEMISTRY, ORGANIC Beilstein Journal of Organic Chemistry Pub Date : 2024-09-30 eCollection Date: 2024-01-01 DOI:10.3762/bjoc.20.209
Smaher E Butt, Konrad Kepski, Jean-Marc Sotiropoulos, Wesley J Moran
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Abstract

A change in mechanism was observed in the hypervalent iodine-mediated cyclization of N-alkenylamides when the carbon chain between the alkene and the amide increased from two to three atoms. In the latter case, cyclization at the amide nitrogen to form the pyrrolidine ring was favored over cyclization at the amide oxygen. A DFT study was undertaken to rationalize the change in mechanism of this cyclization process. In addition, reaction conditions were developed, and the scope of this cyclization studied.

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高价碘介导的双烯丙基酰胺环化生成脯氨醇。
当烯和酰胺之间的碳链从两个原子增加到三个原子时,在高价碘介导的 N-烯酰胺环化过程中观察到机制发生了变化。在后一种情况下,酰胺氮处的环化形成吡咯烷环比酰胺氧处的环化更有利。为了合理解释这一环化过程的机理变化,我们进行了一项 DFT 研究。此外,还制定了反应条件,并研究了这种环化的范围。
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
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.
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