nhc键合异苯并呋喃[10π+2π]环加成对映选择性构建螺虫吲哚-γ-丁内酯

IF 5.5 1区化学 Q2 CHEMISTRY, MULTIDISCIPLINARY

Chinese Journal of Chemistry Pub Date : 2025-05-12 DOI:10.1002/cjoc.70071

Shuixiu Su, Ying Chen, Qiyu Wang, Jian Zhang, Yang-Zi Liu, Wei-Ping Deng

{"title":"nhc键合异苯并呋喃[10π+2π]环加成对映选择性构建螺虫吲哚-γ-丁内酯","authors":"Shuixiu Su, Ying Chen, Qiyu Wang, Jian Zhang, Yang-Zi Liu, Wei-Ping Deng","doi":"10.1002/cjoc.70071","DOIUrl":null,"url":null,"abstract":"<div>\n \n <p>We report an <i>N</i>-heterocyclic carbene (NHC)-catalyzed [10π+2π] cycloaddition between indene-2-carbaldehydes and isatins, delivering spirooxindole-γ-butyrolactones with moderate yields (up to 68%) and excellent enantioselectivity (up to 93% ee). This transformation proceeds via NHC-bound isobenzofulvene intermediates and represents the first successful application of all-carbon higherene in NHC-catalyzed [10π+2π] cycloadditions.</p>\n <p>\n </p>\n </div>","PeriodicalId":151,"journal":{"name":"Chinese Journal of Chemistry","volume":"43 16","pages":"1983-1987"},"PeriodicalIF":5.5000,"publicationDate":"2025-05-12","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":"0","resultStr":"{\"title\":\"Enantioselective Construction of Spirooxindole-γ-butyrolactones via NHC-Bound Isobenzofulvene [10π+2π] Cycloaddition\",\"authors\":\"Shuixiu Su, Ying Chen, Qiyu Wang, Jian Zhang, Yang-Zi Liu, Wei-Ping Deng\",\"doi\":\"10.1002/cjoc.70071\",\"DOIUrl\":null,\"url\":null,\"abstract\":\"<div>\\n \\n <p>We report an <i>N</i>-heterocyclic carbene (NHC)-catalyzed [10π+2π] cycloaddition between indene-2-carbaldehydes and isatins, delivering spirooxindole-γ-butyrolactones with moderate yields (up to 68%) and excellent enantioselectivity (up to 93% ee). This transformation proceeds via NHC-bound isobenzofulvene intermediates and represents the first successful application of all-carbon higherene in NHC-catalyzed [10π+2π] cycloadditions.</p>\\n <p>\\n </p>\\n </div>\",\"PeriodicalId\":151,\"journal\":{\"name\":\"Chinese Journal of Chemistry\",\"volume\":\"43 16\",\"pages\":\"1983-1987\"},\"PeriodicalIF\":5.5000,\"publicationDate\":\"2025-05-12\",\"publicationTypes\":\"Journal Article\",\"fieldsOfStudy\":null,\"isOpenAccess\":false,\"openAccessPdf\":\"\",\"citationCount\":\"0\",\"resultStr\":null,\"platform\":\"Semanticscholar\",\"paperid\":null,\"PeriodicalName\":\"Chinese Journal of Chemistry\",\"FirstCategoryId\":\"92\",\"ListUrlMain\":\"https://onlinelibrary.wiley.com/doi/10.1002/cjoc.70071\",\"RegionNum\":1,\"RegionCategory\":\"化学\",\"ArticlePicture\":[],\"TitleCN\":null,\"AbstractTextCN\":null,\"PMCID\":null,\"EPubDate\":\"\",\"PubModel\":\"\",\"JCR\":\"Q2\",\"JCRName\":\"CHEMISTRY, MULTIDISCIPLINARY\",\"Score\":null,\"Total\":0}","platform":"Semanticscholar","paperid":null,"PeriodicalName":"Chinese Journal of Chemistry","FirstCategoryId":"92","ListUrlMain":"https://onlinelibrary.wiley.com/doi/10.1002/cjoc.70071","RegionNum":1,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":null,"EPubDate":"","PubModel":"","JCR":"Q2","JCRName":"CHEMISTRY, MULTIDISCIPLINARY","Score":null,"Total":0}

引用次数: 0

摘要

我们报道了一种n -杂环碳烯（NHC）催化的茚-2-乙醛和isatins之间的[10π+2π]环加成反应，以中等收率（高达68%）和优异的对映选择性（高达93% ee）产生螺肟吲哚-γ-丁内酯。这种转化是通过nhc结合的异苯并呋喃中间体进行的，代表了全碳高烯在nhc催化的[10π+2π]环加成中的首次成功应用。

本文章由计算机程序翻译，如有差异，请以英文原文为准。

查看原文本刊更多论文

Enantioselective Construction of Spirooxindole-γ-butyrolactones via NHC-Bound Isobenzofulvene [10π+2π] Cycloaddition

We report an N-heterocyclic carbene (NHC)-catalyzed [10π+2π] cycloaddition between indene-2-carbaldehydes and isatins, delivering spirooxindole-γ-butyrolactones with moderate yields (up to 68%) and excellent enantioselectivity (up to 93% ee). This transformation proceeds via NHC-bound isobenzofulvene intermediates and represents the first successful application of all-carbon higherene in NHC-catalyzed [10π+2π] cycloadditions.

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

Chinese Journal of Chemistry 化学-化学综合

CiteScore

8.80

自引率

14.80%

发文量

422

审稿时长

1.7 months

期刊介绍： The Chinese Journal of Chemistry is an international forum for peer-reviewed original research results in all fields of chemistry. Founded in 1983 under the name Acta Chimica Sinica English Edition and renamed in 1990 as Chinese Journal of Chemistry, the journal publishes a stimulating mixture of Accounts, Full Papers, Notes and Communications in English.