N. O. Ilchenko, D. V. Sudarikov, R. V. Rumyantcev, S. A. Rubtsova, A. V. Kutchin
{"title":"Synthesis of methylated and trifluoromethylated hydroxy thiols based on myrtenal","authors":"N. O. Ilchenko, D. V. Sudarikov, R. V. Rumyantcev, S. A. Rubtsova, A. V. Kutchin","doi":"10.1007/s11172-024-4470-9","DOIUrl":null,"url":null,"abstract":"<div><p>A new method was developed for the stereoselective synthesis of methylated and trifluoromethylated thiols based on (1<i>R</i>)-(–)-myrtenal. The CF<sub>3</sub>-substituted ketone and CH<sub>3</sub>-substituted thioacetate, which are required for the synthesis of the corresponding thiols, were prepared for the first time in 83% and 73% yields, respectively. The yields of CH<sub>3</sub>- and CF<sub>3</sub>-substituted thiols are 70% (<i>de</i> >99%) and 53% (<i>de</i> >99%) after two steps, respectively.</p></div>","PeriodicalId":756,"journal":{"name":"Russian Chemical Bulletin","volume":"73 12","pages":"3593 - 3600"},"PeriodicalIF":1.7000,"publicationDate":"2025-02-20","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":"0","resultStr":null,"platform":"Semanticscholar","paperid":null,"PeriodicalName":"Russian Chemical Bulletin","FirstCategoryId":"92","ListUrlMain":"https://link.springer.com/article/10.1007/s11172-024-4470-9","RegionNum":4,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":null,"EPubDate":"","PubModel":"","JCR":"Q3","JCRName":"CHEMISTRY, MULTIDISCIPLINARY","Score":null,"Total":0}
引用次数: 0
Abstract
A new method was developed for the stereoselective synthesis of methylated and trifluoromethylated thiols based on (1R)-(–)-myrtenal. The CF3-substituted ketone and CH3-substituted thioacetate, which are required for the synthesis of the corresponding thiols, were prepared for the first time in 83% and 73% yields, respectively. The yields of CH3- and CF3-substituted thiols are 70% (de >99%) and 53% (de >99%) after two steps, respectively.
期刊介绍:
Publishing nearly 500 original articles a year, by leading Scientists from Russia and throughout the world, Russian Chemical Bulletin is a prominent international journal. The coverage of the journal spans practically all areas of fundamental chemical research and is presented in five sections:
General and Inorganic Chemistry;
Physical Chemistry;
Organic Chemistry;
Organometallic Chemistry;
Chemistry of Natural Compounds and Bioorganic Chemistry.