C. L. Li, S. Y. Wang, M. R. Zhan, C. C. Chen, Z. X. Wang
{"title":"Synthesis of (S)-2-{(R)-Hydroxy[2-(trifluoromethyl)phenyl]methyl}cyclohexan-1-one Using (1R,2R)-2-(Piperidin-1-yl)cyclohexan-1-amine as a Catalyst","authors":"C. L. Li, S. Y. Wang, M. R. Zhan, C. C. Chen, Z. X. Wang","doi":"10.1134/S1070428024100166","DOIUrl":null,"url":null,"abstract":"<p>Chiral monosubstituted cyclohexanediamine catalyst, namely (1<i>R</i>,2<i>R</i>)-2-(piperidin-1-yl)cyclohexan-1-amine (<b>Cat1</b>) has been efficiently synthesized and used to catalyze the aldol reaction of cyclohexanone and 2-(trifluoromethyl)benzaldehyde to obtain (<i>R</i>)-2-{(<i>S</i>)-hydroxy[2-(trifluoromethyl)phenyl]methyl}cyclohexan-1-one. The catalyst (20 mol %) provided high yield (up to 85%) and excellent enantioselectivity (95.6% <i>ee</i>) in water solution in three parallel tests.</p>","PeriodicalId":766,"journal":{"name":"Russian Journal of Organic Chemistry","volume":"60 10","pages":"1999 - 2003"},"PeriodicalIF":0.8000,"publicationDate":"2024-12-19","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":"0","resultStr":null,"platform":"Semanticscholar","paperid":null,"PeriodicalName":"Russian Journal of Organic Chemistry","FirstCategoryId":"92","ListUrlMain":"https://link.springer.com/article/10.1134/S1070428024100166","RegionNum":4,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":null,"EPubDate":"","PubModel":"","JCR":"Q4","JCRName":"CHEMISTRY, ORGANIC","Score":null,"Total":0}
引用次数: 0
Abstract
Chiral monosubstituted cyclohexanediamine catalyst, namely (1R,2R)-2-(piperidin-1-yl)cyclohexan-1-amine (Cat1) has been efficiently synthesized and used to catalyze the aldol reaction of cyclohexanone and 2-(trifluoromethyl)benzaldehyde to obtain (R)-2-{(S)-hydroxy[2-(trifluoromethyl)phenyl]methyl}cyclohexan-1-one. The catalyst (20 mol %) provided high yield (up to 85%) and excellent enantioselectivity (95.6% ee) in water solution in three parallel tests.
期刊介绍：
Russian Journal of Organic Chemistry is an international peer reviewed journal that covers all aspects of modern organic chemistry including organic synthesis, theoretical organic chemistry, structure and mechanism, and the application of organometallic compounds in organic synthesis.
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