Teng Hu , Yuxuan Zhao , Xiaoyan Luo , Zhong Li , Wu-Lin Yang
{"title":"布氏酸催化 [4 + 2] 环加成法合成具有抗真菌活性的双苯甲酮类螺环酮类化合物。","authors":"Teng Hu , Yuxuan Zhao , Xiaoyan Luo , Zhong Li , Wu-Lin Yang","doi":"10.1039/d4ob00584h","DOIUrl":null,"url":null,"abstract":"<div><p>The intermolecular [4 + 2] cycloaddition of <em>o</em>-hydroxy benzyl alcohols with isochroman ketals was realized by CF<sub>3</sub>CO<sub>2</sub>H catalysis. A broad range of bisbenzannulated [6,6]-spiroketals were formed under the metal-free mild conditions in moderate to excellent yields (45–98%) with mostly excellent diastereoselectivities (up to >20 : 1 dr). Furthermore, the enantioselective version was also preliminarily investigated and the bisbenzannulated [6,6]-spiroketal was obtained with 61% ee in the presence of Sc(OTf)<sub>3</sub>/Feng's chiral <em>N</em>,<em>N</em>′-dioxide ligand. Some of the bisbenzannulated [6,6]-spiroketal products showed good <em>in vitro</em> antifungal activities against <em>Sclerotinia sclerotiorum</em> and <em>Rhizoctonia solani</em>.</p></div>","PeriodicalId":96,"journal":{"name":"Organic & Biomolecular Chemistry","volume":"22 23","pages":"Pages 4656-4661"},"PeriodicalIF":2.7000,"publicationDate":"2024-06-12","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":"0","resultStr":"{\"title\":\"Brønsted acid catalyzed [4 + 2] cycloaddition for the synthesis of bisbenzannulated spiroketals with antifungal activities†\",\"authors\":\"Teng Hu , Yuxuan Zhao , Xiaoyan Luo , Zhong Li , Wu-Lin Yang\",\"doi\":\"10.1039/d4ob00584h\",\"DOIUrl\":null,\"url\":null,\"abstract\":\"<div><p>The intermolecular [4 + 2] cycloaddition of <em>o</em>-hydroxy benzyl alcohols with isochroman ketals was realized by CF<sub>3</sub>CO<sub>2</sub>H catalysis. A broad range of bisbenzannulated [6,6]-spiroketals were formed under the metal-free mild conditions in moderate to excellent yields (45–98%) with mostly excellent diastereoselectivities (up to >20 : 1 dr). Furthermore, the enantioselective version was also preliminarily investigated and the bisbenzannulated [6,6]-spiroketal was obtained with 61% ee in the presence of Sc(OTf)<sub>3</sub>/Feng's chiral <em>N</em>,<em>N</em>′-dioxide ligand. Some of the bisbenzannulated [6,6]-spiroketal products showed good <em>in vitro</em> antifungal activities against <em>Sclerotinia sclerotiorum</em> and <em>Rhizoctonia solani</em>.</p></div>\",\"PeriodicalId\":96,\"journal\":{\"name\":\"Organic & Biomolecular Chemistry\",\"volume\":\"22 23\",\"pages\":\"Pages 4656-4661\"},\"PeriodicalIF\":2.7000,\"publicationDate\":\"2024-06-12\",\"publicationTypes\":\"Journal Article\",\"fieldsOfStudy\":null,\"isOpenAccess\":false,\"openAccessPdf\":\"\",\"citationCount\":\"0\",\"resultStr\":null,\"platform\":\"Semanticscholar\",\"paperid\":null,\"PeriodicalName\":\"Organic & Biomolecular Chemistry\",\"FirstCategoryId\":\"92\",\"ListUrlMain\":\"https://www.sciencedirect.com/org/science/article/pii/S1477052024004828\",\"RegionNum\":3,\"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 & Biomolecular Chemistry","FirstCategoryId":"92","ListUrlMain":"https://www.sciencedirect.com/org/science/article/pii/S1477052024004828","RegionNum":3,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":null,"EPubDate":"","PubModel":"","JCR":"Q1","JCRName":"CHEMISTRY, ORGANIC","Score":null,"Total":0}
Brønsted acid catalyzed [4 + 2] cycloaddition for the synthesis of bisbenzannulated spiroketals with antifungal activities†
The intermolecular [4 + 2] cycloaddition of o-hydroxy benzyl alcohols with isochroman ketals was realized by CF3CO2H catalysis. A broad range of bisbenzannulated [6,6]-spiroketals were formed under the metal-free mild conditions in moderate to excellent yields (45–98%) with mostly excellent diastereoselectivities (up to >20 : 1 dr). Furthermore, the enantioselective version was also preliminarily investigated and the bisbenzannulated [6,6]-spiroketal was obtained with 61% ee in the presence of Sc(OTf)3/Feng's chiral N,N′-dioxide ligand. Some of the bisbenzannulated [6,6]-spiroketal products showed good in vitro antifungal activities against Sclerotinia sclerotiorum and Rhizoctonia solani.
期刊介绍:
Organic & Biomolecular Chemistry is an international journal using integrated research in chemistry-organic chemistry. Founded in 2003 by the Royal Society of Chemistry, the journal is published in Semimonthly issues and has been indexed by SCIE, a leading international database. The journal focuses on the key research and cutting-edge progress in the field of chemistry-organic chemistry, publishes and reports the research results in this field in a timely manner, and is committed to becoming a window and platform for rapid academic exchanges among peers in this field. The journal's impact factor in 2023 is 2.9, and its CiteScore is 5.5.