3-spiropiperidines 的不对称 "Clip-Cycle "合成。

IF 2.7 3区 化学 Q1 CHEMISTRY, ORGANIC Organic & Biomolecular Chemistry Pub Date : 2024-11-04 Epub Date: 2024-11-20 DOI:10.1039/d4ob01608d
Saikiran Ravi , Christopher J. Maddocks , Ian J. S. Fairlamb , William P. Unsworth , Paul A. Clarke
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引用次数: 0

摘要

采用两步 "剪切循环 "法合成 3-表哌啶类化合物,收率高达 87%,产率为 96 :4 er。该方法的 "剪切 "阶段基于 N-Cbz 保护的 1-ino-hex-5-enes 与硫代丙烯酸酯的高效、高 E 选择性交叉偏析。随后是 "循环 "步骤,在这一步骤中,手性磷酸催化剂促进了分子内不对称氮杂迈克尔环化反应。
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Asymmetric ‘Clip-Cycle’ synthesis of 3-spiropiperidines†
3-Spiropiperidines can be synthesized in up to 87% yield and 96 : 4 er using a two step ‘Clip-Cycle’ approach. The ‘Clip’ stage of this method is based on efficient and highly E-selective cross metathesis of N-Cbz-protected 1-amino-hex-5-enes with a thioacrylate. This is followed by the ‘Cycle’ step, in which an intramolecular asymmetric aza-Michael cyclization is promoted by a chiral phosphoric acid catalyst.
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来源期刊
Organic & Biomolecular Chemistry
Organic & Biomolecular Chemistry 化学-有机化学
CiteScore
5.50
自引率
9.40%
发文量
1056
审稿时长
1.3 months
期刊介绍: Organic & Biomolecular Chemistry is an international journal using integrated research in chemistry-organic chemistry. Founded in 2003 by the Royal Society of Chemistry, the journal is published in Semimonthly issues and has been indexed by SCIE, a leading international database. The journal focuses on the key research and cutting-edge progress in the field of chemistry-organic chemistry, publishes and reports the research results in this field in a timely manner, and is committed to becoming a window and platform for rapid academic exchanges among peers in this field. The journal's impact factor in 2023 is 2.9, and its CiteScore is 5.5.
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