Qinqin Cui , Shouang Lan , Xiang Lei , Chao Xu , Chunyun Jiang , Lili Zhao , Liyuan Zhou , Jinggong Liu , Cheng-Zhi Gu , Shuang Yang , Xinqiang Fang
{"title":"铜催化clok - wilson重排合成含四取代碳原子的二氢呋喃","authors":"Qinqin Cui , Shouang Lan , Xiang Lei , Chao Xu , Chunyun Jiang , Lili Zhao , Liyuan Zhou , Jinggong Liu , Cheng-Zhi Gu , Shuang Yang , Xinqiang Fang","doi":"10.1039/d5qo00401b","DOIUrl":null,"url":null,"abstract":"<div><div>The Cloke–Wilson rearrangement is a well-established method for synthesizing dihydrofurans, but it primarily results in dihydrofurans lacking tetrasubstituted carbon atoms. In this study, we introduce a copper-catalyzed variant of the Cloke–Wilson rearrangement that utilizes 1,1,2,2-tetrasubstituted cyclopropanes. This approach allows for the synthesis of a diverse range of dihydrofurans featuring tetrasubstituted carbon atoms, with yields ranging from good to excellent.</div></div>","PeriodicalId":94379,"journal":{"name":"Organic chemistry frontiers : an international journal of organic chemistry","volume":"12 18","pages":"Pages 5051-5057"},"PeriodicalIF":0.0000,"publicationDate":"2025-04-26","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":"0","resultStr":"{\"title\":\"Copper-catalyzed Cloke–Wilson rearrangement for the synthesis of dihydrofurans containing tetrasubstituted carbon atoms†\",\"authors\":\"Qinqin Cui , Shouang Lan , Xiang Lei , Chao Xu , Chunyun Jiang , Lili Zhao , Liyuan Zhou , Jinggong Liu , Cheng-Zhi Gu , Shuang Yang , Xinqiang Fang\",\"doi\":\"10.1039/d5qo00401b\",\"DOIUrl\":null,\"url\":null,\"abstract\":\"<div><div>The Cloke–Wilson rearrangement is a well-established method for synthesizing dihydrofurans, but it primarily results in dihydrofurans lacking tetrasubstituted carbon atoms. In this study, we introduce a copper-catalyzed variant of the Cloke–Wilson rearrangement that utilizes 1,1,2,2-tetrasubstituted cyclopropanes. This approach allows for the synthesis of a diverse range of dihydrofurans featuring tetrasubstituted carbon atoms, with yields ranging from good to excellent.</div></div>\",\"PeriodicalId\":94379,\"journal\":{\"name\":\"Organic chemistry frontiers : an international journal of organic chemistry\",\"volume\":\"12 18\",\"pages\":\"Pages 5051-5057\"},\"PeriodicalIF\":0.0000,\"publicationDate\":\"2025-04-26\",\"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/S2052412925003298\",\"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/S2052412925003298","RegionNum":0,"RegionCategory":null,"ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":null,"EPubDate":"","PubModel":"","JCR":"","JCRName":"","Score":null,"Total":0}
Copper-catalyzed Cloke–Wilson rearrangement for the synthesis of dihydrofurans containing tetrasubstituted carbon atoms†
The Cloke–Wilson rearrangement is a well-established method for synthesizing dihydrofurans, but it primarily results in dihydrofurans lacking tetrasubstituted carbon atoms. In this study, we introduce a copper-catalyzed variant of the Cloke–Wilson rearrangement that utilizes 1,1,2,2-tetrasubstituted cyclopropanes. This approach allows for the synthesis of a diverse range of dihydrofurans featuring tetrasubstituted carbon atoms, with yields ranging from good to excellent.