底物和试剂控制的乙烯基对醌二聚化反应

IF 3.3 2区化学 Q1 CHEMISTRY, ORGANIC

Journal of Organic Chemistry Pub Date : 2025-04-21 DOI:10.1021/acs.joc.5c0012310.1021/acs.joc.5c00123

Ryan G. Baker, Kyle D. Reichl, Michael J. Smith, Michael Ricca, Margaret A. Mickelberg and John A. Porco Jr.*,

{"title":"底物和试剂控制的乙烯基对醌二聚化反应","authors":"Ryan G. Baker, Kyle D. Reichl, Michael J. Smith, Michael Ricca, Margaret A. Mickelberg and John A. Porco Jr.*, ","doi":"10.1021/acs.joc.5c0012310.1021/acs.joc.5c00123","DOIUrl":null,"url":null,"abstract":"Substrate and reagent-controlled dimerization of vinyl para-quinone methides (VPQMs) is reported. When subjected to Brønsted acidic conditions, VPQM dimerization occurs via a formal 1,8-addition to provide griffipavixanthone (GPX)-type congeners. Under optimized Lewis acidic conditions, a change in regioselectivity affords limonene-containing dimers by a 1,6-addition/cyclization process. This divergent reactivity has been explored on several substrates of differing complexity, providing access to analogues of the natural product griffipavixanthone (GPX) as well as a range of novel, substituted limonene dimers.","PeriodicalId":57,"journal":{"name":"Journal of Organic Chemistry","volume":"90 17","pages":"5871–5889 5871–5889"},"PeriodicalIF":3.3000,"publicationDate":"2025-04-21","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":"0","resultStr":"{\"title\":\"Substrate- and Reagent-Controlled Dimerization of Vinyl para-Quinone Methides\",\"authors\":\"Ryan G. Baker, Kyle D. Reichl, Michael J. Smith, Michael Ricca, Margaret A. Mickelberg and John A. Porco Jr.*, \",\"doi\":\"10.1021/acs.joc.5c0012310.1021/acs.joc.5c00123\",\"DOIUrl\":null,\"url\":null,\"abstract\":\"Substrate and reagent-controlled dimerization of vinyl para-quinone methides (VPQMs) is reported. When subjected to Brønsted acidic conditions, VPQM dimerization occurs via a formal 1,8-addition to provide griffipavixanthone (GPX)-type congeners. Under optimized Lewis acidic conditions, a change in regioselectivity affords limonene-containing dimers by a 1,6-addition/cyclization process. This divergent reactivity has been explored on several substrates of differing complexity, providing access to analogues of the natural product griffipavixanthone (GPX) as well as a range of novel, substituted limonene dimers.\",\"PeriodicalId\":57,\"journal\":{\"name\":\"Journal of Organic Chemistry\",\"volume\":\"90 17\",\"pages\":\"5871–5889 5871–5889\"},\"PeriodicalIF\":3.3000,\"publicationDate\":\"2025-04-21\",\"publicationTypes\":\"Journal Article\",\"fieldsOfStudy\":null,\"isOpenAccess\":false,\"openAccessPdf\":\"\",\"citationCount\":\"0\",\"resultStr\":null,\"platform\":\"Semanticscholar\",\"paperid\":null,\"PeriodicalName\":\"Journal of Organic Chemistry\",\"FirstCategoryId\":\"1\",\"ListUrlMain\":\"https://pubs.acs.org/doi/10.1021/acs.joc.5c00123\",\"RegionNum\":2,\"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":"Journal of Organic Chemistry","FirstCategoryId":"1","ListUrlMain":"https://pubs.acs.org/doi/10.1021/acs.joc.5c00123","RegionNum":2,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":null,"EPubDate":"","PubModel":"","JCR":"Q1","JCRName":"CHEMISTRY, ORGANIC","Score":null,"Total":0}

引用次数: 0

摘要

报道了底物和试剂控制的乙烯基对苯二酚二聚化反应。当受到Brønsted酸性条件时，VPQM通过正式的1,8加成发生二聚化，以提供griffipavixanthone （GPX）型同源物。在优化的Lewis酸条件下，区域选择性的变化通过1,6加成/环化过程提供了含柠檬烯二聚体。这种不同的反应性已经在几种不同复杂性的底物上进行了探索，提供了天然产物griffipavixanthone （GPX）的类似物以及一系列新颖的取代柠檬烯二聚体。

本文章由计算机程序翻译，如有差异，请以英文原文为准。

Substrate- and Reagent-Controlled Dimerization of Vinyl para-Quinone Methides

查看原文本刊更多论文

Substrate- and Reagent-Controlled Dimerization of Vinyl para-Quinone Methides

Substrate and reagent-controlled dimerization of vinyl para-quinone methides (VPQMs) is reported. When subjected to Brønsted acidic conditions, VPQM dimerization occurs via a formal 1,8-addition to provide griffipavixanthone (GPX)-type congeners. Under optimized Lewis acidic conditions, a change in regioselectivity affords limonene-containing dimers by a 1,6-addition/cyclization process. This divergent reactivity has been explored on several substrates of differing complexity, providing access to analogues of the natural product griffipavixanthone (GPX) as well as a range of novel, substituted limonene dimers.

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

Journal of Organic Chemistry 化学-有机化学

CiteScore

6.20

自引率

11.10%

发文量

1467

审稿时长

2 months

期刊介绍： Journal of Organic Chemistry welcomes original contributions of fundamental research in all branches of the theory and practice of organic chemistry. In selecting manuscripts for publication, the editors place emphasis on the quality and novelty of the work, as well as the breadth of interest to the organic chemistry community.