{"title":"通过Friedel-Crafts烷基化/环化不对称合成7-元环桥3,4-氟三环吲哚†","authors":"Bai-Yu Xue , Chen-Ying Hou , Xiao-Bing Wang , Ming-Sheng Xie , Hai-Ming Guo","doi":"10.1039/d2qo01982e","DOIUrl":null,"url":null,"abstract":"<div><p>With <em>N</em>-methyl-4-aminoindole as the 1,4-bisnucleophile, the regio- and enantioselective Friedel–Crafts alkylation/<em>N</em>-hemiacetalization and dehydration sequence with β,γ-unsaturated α-ketoesters was reported using 5 mol% Ni(<span>ii</span>)-PyBPI complex, affording diverse chiral 7-membered-ring-bridged 3,4-fused tricyclic indoles in good results (up to 91% yield and 97% ee). The by-products were 6-membered-ring-bridged 4,5-fused tricyclic indoles.</p></div>","PeriodicalId":94379,"journal":{"name":"Organic chemistry frontiers : an international journal of organic chemistry","volume":"10 8","pages":"Pages 1910-1914"},"PeriodicalIF":0.0000,"publicationDate":"2023-01-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":"0","resultStr":"{\"title\":\"Asymmetric synthesis of 7-membered-ring-bridged 3,4-fused tricyclic indoles via Friedel–Crafts alkylation/annulation†\",\"authors\":\"Bai-Yu Xue , Chen-Ying Hou , Xiao-Bing Wang , Ming-Sheng Xie , Hai-Ming Guo\",\"doi\":\"10.1039/d2qo01982e\",\"DOIUrl\":null,\"url\":null,\"abstract\":\"<div><p>With <em>N</em>-methyl-4-aminoindole as the 1,4-bisnucleophile, the regio- and enantioselective Friedel–Crafts alkylation/<em>N</em>-hemiacetalization and dehydration sequence with β,γ-unsaturated α-ketoesters was reported using 5 mol% Ni(<span>ii</span>)-PyBPI complex, affording diverse chiral 7-membered-ring-bridged 3,4-fused tricyclic indoles in good results (up to 91% yield and 97% ee). The by-products were 6-membered-ring-bridged 4,5-fused tricyclic indoles.</p></div>\",\"PeriodicalId\":94379,\"journal\":{\"name\":\"Organic chemistry frontiers : an international journal of organic chemistry\",\"volume\":\"10 8\",\"pages\":\"Pages 1910-1914\"},\"PeriodicalIF\":0.0000,\"publicationDate\":\"2023-01-01\",\"publicationTypes\":\"Journal Article\",\"fieldsOfStudy\":null,\"isOpenAccess\":false,\"openAccessPdf\":\"\",\"citationCount\":\"0\",\"resultStr\":null,\"platform\":\"Semanticscholar\",\"paperid\":null,\"PeriodicalName\":\"Organic chemistry frontiers : an international journal of organic chemistry\",\"FirstCategoryId\":\"1085\",\"ListUrlMain\":\"https://www.sciencedirect.com/org/science/article/pii/S2052411023006041\",\"RegionNum\":0,\"RegionCategory\":null,\"ArticlePicture\":[],\"TitleCN\":null,\"AbstractTextCN\":null,\"PMCID\":null,\"EPubDate\":\"\",\"PubModel\":\"\",\"JCR\":\"\",\"JCRName\":\"\",\"Score\":null,\"Total\":0}","platform":"Semanticscholar","paperid":null,"PeriodicalName":"Organic chemistry frontiers : an international journal of organic chemistry","FirstCategoryId":"1085","ListUrlMain":"https://www.sciencedirect.com/org/science/article/pii/S2052411023006041","RegionNum":0,"RegionCategory":null,"ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":null,"EPubDate":"","PubModel":"","JCR":"","JCRName":"","Score":null,"Total":0}
Asymmetric synthesis of 7-membered-ring-bridged 3,4-fused tricyclic indoles via Friedel–Crafts alkylation/annulation†
With N-methyl-4-aminoindole as the 1,4-bisnucleophile, the regio- and enantioselective Friedel–Crafts alkylation/N-hemiacetalization and dehydration sequence with β,γ-unsaturated α-ketoesters was reported using 5 mol% Ni(ii)-PyBPI complex, affording diverse chiral 7-membered-ring-bridged 3,4-fused tricyclic indoles in good results (up to 91% yield and 97% ee). The by-products were 6-membered-ring-bridged 4,5-fused tricyclic indoles.
京公网安备 11010802042870号
京ICP备2023020795号-1
分享
求助内容：
应助结果提醒方式：
扫码关注我们
