Meiwen Liu, Yihao Zhang, Xin-Yan Ke, Shao-Fei Ni and Pengfei Li*,
{"title":"原位形成的烷基8-亚甲基萘-2(8H)- 1的不对称有机催化1,6-共轭加成：轴向和中心手性的协同构建","authors":"Meiwen Liu, Yihao Zhang, Xin-Yan Ke, Shao-Fei Ni and Pengfei Li*, ","doi":"10.1021/acs.orglett.4c0486410.1021/acs.orglett.4c04864","DOIUrl":null,"url":null,"abstract":"<p >Organocatalytic enantioselective formal nucleophilic substitution reactions of α-(2-hydroxynaphthalen-8-yl)propargyl alcohols with 1-(1<i>H</i>-indol-3-yl)naphthalen-2-ols have been established for the first time. With the aid of a suitable chiral phosphoric acid, alkynyl 8-methylenenaphthalen-2(8<i>H</i>)-one was formed in situ from the corresponding α-(2-hydroxynaphthalen-8-yl)propargyl alcohol, followed by enantioselective 1,6-conjugate additions of 1-(1<i>H</i>-indol-3-yl)naphthalen-2-ols to afford a number of enantioenriched (<i>R</i><sub><i>a</i></sub>,<i>S</i><sub><i>c</i></sub>)-2,3-disubstituted indoles in 50–80% yields with 81–93% ee and (<i>S</i><sub><i>a</i></sub>,<i>S</i><sub><i>c</i></sub>)-2,3-disubstituted indoles in 18–40% yields with 79–96% ee. Notably, these nucleophilic substitution products were characterized by the presence of functional groups, including indole, naphthol, and alkynyl units, while exhibiting both axial and central chirality.</p>","PeriodicalId":54,"journal":{"name":"Organic Letters","volume":"27 5","pages":"1271–1275 1271–1275"},"PeriodicalIF":5.0000,"publicationDate":"2025-01-26","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":"0","resultStr":"{\"title\":\"Asymmetric Organocatalytic 1,6-Conjugate Addition of Alkynyl 8-Methylenenaphthalen-2(8H)-one Formed In Situ: Synergistic Construction of Axial and Central Chirality\",\"authors\":\"Meiwen Liu, Yihao Zhang, Xin-Yan Ke, Shao-Fei Ni and Pengfei Li*, \",\"doi\":\"10.1021/acs.orglett.4c0486410.1021/acs.orglett.4c04864\",\"DOIUrl\":null,\"url\":null,\"abstract\":\"<p >Organocatalytic enantioselective formal nucleophilic substitution reactions of α-(2-hydroxynaphthalen-8-yl)propargyl alcohols with 1-(1<i>H</i>-indol-3-yl)naphthalen-2-ols have been established for the first time. With the aid of a suitable chiral phosphoric acid, alkynyl 8-methylenenaphthalen-2(8<i>H</i>)-one was formed in situ from the corresponding α-(2-hydroxynaphthalen-8-yl)propargyl alcohol, followed by enantioselective 1,6-conjugate additions of 1-(1<i>H</i>-indol-3-yl)naphthalen-2-ols to afford a number of enantioenriched (<i>R</i><sub><i>a</i></sub>,<i>S</i><sub><i>c</i></sub>)-2,3-disubstituted indoles in 50–80% yields with 81–93% ee and (<i>S</i><sub><i>a</i></sub>,<i>S</i><sub><i>c</i></sub>)-2,3-disubstituted indoles in 18–40% yields with 79–96% ee. Notably, these nucleophilic substitution products were characterized by the presence of functional groups, including indole, naphthol, and alkynyl units, while exhibiting both axial and central chirality.</p>\",\"PeriodicalId\":54,\"journal\":{\"name\":\"Organic Letters\",\"volume\":\"27 5\",\"pages\":\"1271–1275 1271–1275\"},\"PeriodicalIF\":5.0000,\"publicationDate\":\"2025-01-26\",\"publicationTypes\":\"Journal Article\",\"fieldsOfStudy\":null,\"isOpenAccess\":false,\"openAccessPdf\":\"\",\"citationCount\":\"0\",\"resultStr\":null,\"platform\":\"Semanticscholar\",\"paperid\":null,\"PeriodicalName\":\"Organic Letters\",\"FirstCategoryId\":\"92\",\"ListUrlMain\":\"https://pubs.acs.org/doi/10.1021/acs.orglett.4c04864\",\"RegionNum\":1,\"RegionCategory\":\"化学\",\"ArticlePicture\":[],\"TitleCN\":null,\"AbstractTextCN\":null,\"PMCID\":null,\"EPubDate\":\"\",\"PubModel\":\"\",\"JCR\":\"Q1\",\"JCRName\":\"CHEMISTRY, ORGANIC\",\"Score\":null,\"Total\":0}","platform":"Semanticscholar","paperid":null,"PeriodicalName":"Organic Letters","FirstCategoryId":"92","ListUrlMain":"https://pubs.acs.org/doi/10.1021/acs.orglett.4c04864","RegionNum":1,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":null,"EPubDate":"","PubModel":"","JCR":"Q1","JCRName":"CHEMISTRY, ORGANIC","Score":null,"Total":0}
Asymmetric Organocatalytic 1,6-Conjugate Addition of Alkynyl 8-Methylenenaphthalen-2(8H)-one Formed In Situ: Synergistic Construction of Axial and Central Chirality
Organocatalytic enantioselective formal nucleophilic substitution reactions of α-(2-hydroxynaphthalen-8-yl)propargyl alcohols with 1-(1H-indol-3-yl)naphthalen-2-ols have been established for the first time. With the aid of a suitable chiral phosphoric acid, alkynyl 8-methylenenaphthalen-2(8H)-one was formed in situ from the corresponding α-(2-hydroxynaphthalen-8-yl)propargyl alcohol, followed by enantioselective 1,6-conjugate additions of 1-(1H-indol-3-yl)naphthalen-2-ols to afford a number of enantioenriched (Ra,Sc)-2,3-disubstituted indoles in 50–80% yields with 81–93% ee and (Sa,Sc)-2,3-disubstituted indoles in 18–40% yields with 79–96% ee. Notably, these nucleophilic substitution products were characterized by the presence of functional groups, including indole, naphthol, and alkynyl units, while exhibiting both axial and central chirality.
期刊介绍：
Organic Letters invites original reports of fundamental research in all branches of the theory and practice of organic, physical organic, organometallic,medicinal, and bioorganic chemistry. Organic Letters provides rapid disclosure of the key elements of significant studies that are of interest to a large portion of the organic community. In selecting manuscripts for publication, the Editors place emphasis on the originality, quality and wide interest of the work. Authors should provide enough background information to place the new disclosure in context and to justify the rapid publication format. Back-to-back Letters will be considered. Full details should be reserved for an Article, which should appear in due course.
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