Ti-Mg 与 Et2Zn 催化的 N-苄基-N-(丁-3-烯-1-基)庚-2-炔-1-胺羧锌化反应

IF 0.8 4区 化学 Q4 CHEMISTRY, ORGANIC
A. M. Gabdullin, R. N. Kadikova, I. R. Ramazanov
{"title":"Ti-Mg 与 Et2Zn 催化的 N-苄基-N-(丁-3-烯-1-基)庚-2-炔-1-胺羧锌化反应","authors":"A. M. Gabdullin,&nbsp;R. N. Kadikova,&nbsp;I. R. Ramazanov","doi":"10.1134/S1070428024080049","DOIUrl":null,"url":null,"abstract":"<p>It has been shown for the first time that the Ti-Mg-catalyzed carbozincation reaction of <i>N</i>-benzyl-<i>N</i>-(but-3-en-1-yl)hept-2-yn-1-amine with Et<sub>2</sub>Zn involves the regio- and stereoselective formation of (<i>Z</i>)-1-benzyl-4-methyl-3-pentylidenepiperidine. The effect of the solvent on the Ti-Mg-catalyzed heterocyclization of <i>N</i>-benzyl-<i>N</i>-(but-3-en-1-yl)hept-2-yn-1-amine was studied. A mechanism of the carbozincation of <i>N</i>-homoallyl-substituted propargylamine with Et<sub>2</sub>Zn in the presence of catalytic amounts of Ti(O-<i>i</i>Pr)<sub>4</sub> and EtMgBr has been proposed.</p>","PeriodicalId":766,"journal":{"name":"Russian Journal of Organic Chemistry","volume":"60 8","pages":"1600 - 1606"},"PeriodicalIF":0.8000,"publicationDate":"2024-11-06","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":"0","resultStr":"{\"title\":\"Ti–Mg-Catalyzed Carbozincation of N-Benzyl-N-(but-3-en-1-yl)hept-2-yn-1-amine with Et2Zn\",\"authors\":\"A. M. Gabdullin,&nbsp;R. N. Kadikova,&nbsp;I. R. Ramazanov\",\"doi\":\"10.1134/S1070428024080049\",\"DOIUrl\":null,\"url\":null,\"abstract\":\"<p>It has been shown for the first time that the Ti-Mg-catalyzed carbozincation reaction of <i>N</i>-benzyl-<i>N</i>-(but-3-en-1-yl)hept-2-yn-1-amine with Et<sub>2</sub>Zn involves the regio- and stereoselective formation of (<i>Z</i>)-1-benzyl-4-methyl-3-pentylidenepiperidine. The effect of the solvent on the Ti-Mg-catalyzed heterocyclization of <i>N</i>-benzyl-<i>N</i>-(but-3-en-1-yl)hept-2-yn-1-amine was studied. A mechanism of the carbozincation of <i>N</i>-homoallyl-substituted propargylamine with Et<sub>2</sub>Zn in the presence of catalytic amounts of Ti(O-<i>i</i>Pr)<sub>4</sub> and EtMgBr has been proposed.</p>\",\"PeriodicalId\":766,\"journal\":{\"name\":\"Russian Journal of Organic Chemistry\",\"volume\":\"60 8\",\"pages\":\"1600 - 1606\"},\"PeriodicalIF\":0.8000,\"publicationDate\":\"2024-11-06\",\"publicationTypes\":\"Journal Article\",\"fieldsOfStudy\":null,\"isOpenAccess\":false,\"openAccessPdf\":\"\",\"citationCount\":\"0\",\"resultStr\":null,\"platform\":\"Semanticscholar\",\"paperid\":null,\"PeriodicalName\":\"Russian Journal of Organic Chemistry\",\"FirstCategoryId\":\"92\",\"ListUrlMain\":\"https://link.springer.com/article/10.1134/S1070428024080049\",\"RegionNum\":4,\"RegionCategory\":\"化学\",\"ArticlePicture\":[],\"TitleCN\":null,\"AbstractTextCN\":null,\"PMCID\":null,\"EPubDate\":\"\",\"PubModel\":\"\",\"JCR\":\"Q4\",\"JCRName\":\"CHEMISTRY, ORGANIC\",\"Score\":null,\"Total\":0}","platform":"Semanticscholar","paperid":null,"PeriodicalName":"Russian Journal of Organic Chemistry","FirstCategoryId":"92","ListUrlMain":"https://link.springer.com/article/10.1134/S1070428024080049","RegionNum":4,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":null,"EPubDate":"","PubModel":"","JCR":"Q4","JCRName":"CHEMISTRY, ORGANIC","Score":null,"Total":0}
引用次数: 0

摘要

研究首次表明,N-苄基-N-(丁-3-烯-1-基)庚-2-炔-1-胺与 Et2Zn 的钛-镁催化羧锌化反应涉及 (Z)-1- 苄基-4-甲基-3-亚戊基哌啶的区域和立体选择性生成。研究了溶剂对 Ti-Mg 催化的 N-苄基-N-(丁-3-烯-1-基)庚-2-炔-1-胺杂环化反应的影响。提出了在催化量的 Ti(O-iPr)4 和 EtMgBr 存在下,用 Et2Zn 对 N-高烯丙基取代的丙炔胺进行羧锌化合的机理。
本文章由计算机程序翻译,如有差异,请以英文原文为准。

Ti–Mg-Catalyzed Carbozincation of N-Benzyl-N-(but-3-en-1-yl)hept-2-yn-1-amine with Et2Zn

Ti–Mg-Catalyzed Carbozincation of N-Benzyl-N-(but-3-en-1-yl)hept-2-yn-1-amine with Et2Zn

It has been shown for the first time that the Ti-Mg-catalyzed carbozincation reaction of N-benzyl-N-(but-3-en-1-yl)hept-2-yn-1-amine with Et2Zn involves the regio- and stereoselective formation of (Z)-1-benzyl-4-methyl-3-pentylidenepiperidine. The effect of the solvent on the Ti-Mg-catalyzed heterocyclization of N-benzyl-N-(but-3-en-1-yl)hept-2-yn-1-amine was studied. A mechanism of the carbozincation of N-homoallyl-substituted propargylamine with Et2Zn in the presence of catalytic amounts of Ti(O-iPr)4 and EtMgBr has been proposed.

求助全文
通过发布文献求助,成功后即可免费获取论文全文。 去求助
来源期刊
CiteScore
1.40
自引率
25.00%
发文量
139
审稿时长
3-6 weeks
期刊介绍: Russian Journal of Organic Chemistry is an international peer reviewed journal that covers all aspects of modern organic chemistry including organic synthesis, theoretical organic chemistry, structure and mechanism, and the application of organometallic compounds in organic synthesis.
×
引用
GB/T 7714-2015
复制
MLA
复制
APA
复制
导出至
BibTeX EndNote RefMan NoteFirst NoteExpress
×
提示
您的信息不完整,为了账户安全,请先补充。
现在去补充
×
提示
您因"违规操作"
具体请查看互助需知
我知道了
×
提示
确定
请完成安全验证×
copy
已复制链接
快去分享给好友吧!
我知道了
右上角分享
点击右上角分享
0
联系我们:info@booksci.cn Book学术提供免费学术资源搜索服务,方便国内外学者检索中英文文献。致力于提供最便捷和优质的服务体验。 Copyright © 2023 布克学术 All rights reserved.
京ICP备2023020795号-1
ghs 京公网安备 11010802042870号
Book学术文献互助
Book学术文献互助群
群 号:481959085
Book学术官方微信