{"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, R. N. Kadikova, 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, R. N. Kadikova, 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}
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.
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.