钯催化芳基硼酸和糖烯酮通过1,4-共轭加成反应合成芳基c -糖苷

IF 2.2 4区化学 Q2 CHEMISTRY, ORGANIC

Synthesis-Stuttgart Pub Date : 2023-09-21 DOI:10.1055/a-2179-8669

Jeyakumar Kandasamy, Adesh Kumar Singh, Rapelly Venkatesh

{"title":"钯催化芳基硼酸和糖烯酮通过1,4-共轭加成反应合成芳基c -糖苷","authors":"Jeyakumar Kandasamy, Adesh Kumar Singh, Rapelly Venkatesh","doi":"10.1055/a-2179-8669","DOIUrl":null,"url":null,"abstract":"Abstract 1,4-Conjugate addition of arylboronic acids to the glycal enones delivered 2-deoxy-α-aryl-C-glycosides in good yields. The reaction was catalyzed by palladium acetate in the presence of trifluoroacetic acid and 1,10-phenanthroline. A wide range of glycal enones derived from d-glucal, d-galactal, and d-rhamnal participated in the coupling reaction with different arylboronic acids smoothly. Different protecting groups including benzyl, acetyl, pivaloyl, and benzoyl were compatible under optimized conditions.","PeriodicalId":49451,"journal":{"name":"Synthesis-Stuttgart","volume":"45 1","pages":"0"},"PeriodicalIF":2.2000,"publicationDate":"2023-09-21","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":"0","resultStr":"{\"title\":\"Palladium-Catalyzed Stereocontrolled Synthesis of Aryl-C-Glycosides from Arylboronic Acids and Glycal Enones Through 1,4-Conjugate Addition Reactions\",\"authors\":\"Jeyakumar Kandasamy, Adesh Kumar Singh, Rapelly Venkatesh\",\"doi\":\"10.1055/a-2179-8669\",\"DOIUrl\":null,\"url\":null,\"abstract\":\"Abstract 1,4-Conjugate addition of arylboronic acids to the glycal enones delivered 2-deoxy-α-aryl-C-glycosides in good yields. The reaction was catalyzed by palladium acetate in the presence of trifluoroacetic acid and 1,10-phenanthroline. A wide range of glycal enones derived from d-glucal, d-galactal, and d-rhamnal participated in the coupling reaction with different arylboronic acids smoothly. Different protecting groups including benzyl, acetyl, pivaloyl, and benzoyl were compatible under optimized conditions.\",\"PeriodicalId\":49451,\"journal\":{\"name\":\"Synthesis-Stuttgart\",\"volume\":\"45 1\",\"pages\":\"0\"},\"PeriodicalIF\":2.2000,\"publicationDate\":\"2023-09-21\",\"publicationTypes\":\"Journal Article\",\"fieldsOfStudy\":null,\"isOpenAccess\":false,\"openAccessPdf\":\"\",\"citationCount\":\"0\",\"resultStr\":null,\"platform\":\"Semanticscholar\",\"paperid\":null,\"PeriodicalName\":\"Synthesis-Stuttgart\",\"FirstCategoryId\":\"1085\",\"ListUrlMain\":\"https://doi.org/10.1055/a-2179-8669\",\"RegionNum\":4,\"RegionCategory\":\"化学\",\"ArticlePicture\":[],\"TitleCN\":null,\"AbstractTextCN\":null,\"PMCID\":null,\"EPubDate\":\"\",\"PubModel\":\"\",\"JCR\":\"Q2\",\"JCRName\":\"CHEMISTRY, ORGANIC\",\"Score\":null,\"Total\":0}","platform":"Semanticscholar","paperid":null,"PeriodicalName":"Synthesis-Stuttgart","FirstCategoryId":"1085","ListUrlMain":"https://doi.org/10.1055/a-2179-8669","RegionNum":4,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":null,"EPubDate":"","PubModel":"","JCR":"Q2","JCRName":"CHEMISTRY, ORGANIC","Score":null,"Total":0}

引用次数: 0

摘要

摘要:1,4-芳基硼酸在糖烯酮上的共轭加成可以高产出2-脱氧-α-芳基c -糖苷。在三氟乙酸和1,10-菲罗啉存在下，用醋酸钯催化反应。从d-葡聚糖、d-半乳糖和d-鼠李醛中衍生出的多种糖烯酮可以顺利地与不同的芳基硼酸偶联。在优化条件下，苯、乙酰、戊酰、苯甲酰等不同保护基团均可相容。

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

Palladium-Catalyzed Stereocontrolled Synthesis of Aryl-C-Glycosides from Arylboronic Acids and Glycal Enones Through 1,4-Conjugate Addition Reactions

Abstract 1,4-Conjugate addition of arylboronic acids to the glycal enones delivered 2-deoxy-α-aryl-C-glycosides in good yields. The reaction was catalyzed by palladium acetate in the presence of trifluoroacetic acid and 1,10-phenanthroline. A wide range of glycal enones derived from d-glucal, d-galactal, and d-rhamnal participated in the coupling reaction with different arylboronic acids smoothly. Different protecting groups including benzyl, acetyl, pivaloyl, and benzoyl were compatible under optimized conditions.

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

Synthesis-Stuttgart 化学-有机化学

CiteScore

4.50

自引率

7.70%

发文量

435

审稿时长

1 months

期刊介绍： SYNTHESIS is an international full-paper journal devoted to the advancement of the science of chemical synthesis. It covers all fields of organic chemistry involving synthesis, including catalysis, organometallic, medicinal, biological, and photochemistry, but also related disciplines. SYNTHESIS provides dependable research results with detailed and reliable experimental procedures and full characterization of all important new products as well as scientific primary data.