{"title":"用改性的雷尼镍对CO双键进行对映面分化氢化:加入反应体系的羧酸的作用","authors":"Tadao Harada , Toshihiro Kawamura , Shiro Haikawa , Tsutomu Osawa","doi":"10.1016/0304-5102(94)00090-5","DOIUrl":null,"url":null,"abstract":"<div><p>A tartaric acid—sodium bromide—modified Raney nickel (TANaBrMRNi) is a unique catalyst for the enantioface-differentiating hydrogenation of 2-alkanones and β-ketoesters. The addition of carboxylic acid to the reaction system results in improvement of the optical yield over this catalyst. In this study, the enantioface-differentiating hydrogenations of 2-octanone and methyl acetoacetate were carried out to clarify how the added carboxylic acids improve the efficiency of the enantio-differentiation of the substrates over TANaBrMRNi. The participation of the conjugate bases and protons generated from the added carboxylic acid during the hydrogenation of 2-alkanones and β-ketoesters is proposed.</p></div>","PeriodicalId":16567,"journal":{"name":"分子催化","volume":"93 2","pages":"Pages 211-219"},"PeriodicalIF":0.0000,"publicationDate":"1994-10-13","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"https://sci-hub-pdf.com/10.1016/0304-5102(94)00090-5","citationCount":"13","resultStr":"{\"title\":\"Enantioface-differentiating hydrogenation of the CO double bond using a modified Raney nickel: Role of the carboxylic acid added to the reaction system\",\"authors\":\"Tadao Harada , Toshihiro Kawamura , Shiro Haikawa , Tsutomu Osawa\",\"doi\":\"10.1016/0304-5102(94)00090-5\",\"DOIUrl\":null,\"url\":null,\"abstract\":\"<div><p>A tartaric acid—sodium bromide—modified Raney nickel (TANaBrMRNi) is a unique catalyst for the enantioface-differentiating hydrogenation of 2-alkanones and β-ketoesters. The addition of carboxylic acid to the reaction system results in improvement of the optical yield over this catalyst. In this study, the enantioface-differentiating hydrogenations of 2-octanone and methyl acetoacetate were carried out to clarify how the added carboxylic acids improve the efficiency of the enantio-differentiation of the substrates over TANaBrMRNi. The participation of the conjugate bases and protons generated from the added carboxylic acid during the hydrogenation of 2-alkanones and β-ketoesters is proposed.</p></div>\",\"PeriodicalId\":16567,\"journal\":{\"name\":\"分子催化\",\"volume\":\"93 2\",\"pages\":\"Pages 211-219\"},\"PeriodicalIF\":0.0000,\"publicationDate\":\"1994-10-13\",\"publicationTypes\":\"Journal Article\",\"fieldsOfStudy\":null,\"isOpenAccess\":false,\"openAccessPdf\":\"https://sci-hub-pdf.com/10.1016/0304-5102(94)00090-5\",\"citationCount\":\"13\",\"resultStr\":null,\"platform\":\"Semanticscholar\",\"paperid\":null,\"PeriodicalName\":\"分子催化\",\"FirstCategoryId\":\"1089\",\"ListUrlMain\":\"https://www.sciencedirect.com/science/article/pii/0304510294000905\",\"RegionNum\":0,\"RegionCategory\":null,\"ArticlePicture\":[],\"TitleCN\":null,\"AbstractTextCN\":null,\"PMCID\":null,\"EPubDate\":\"\",\"PubModel\":\"\",\"JCR\":\"Q4\",\"JCRName\":\"Chemical Engineering\",\"Score\":null,\"Total\":0}","platform":"Semanticscholar","paperid":null,"PeriodicalName":"分子催化","FirstCategoryId":"1089","ListUrlMain":"https://www.sciencedirect.com/science/article/pii/0304510294000905","RegionNum":0,"RegionCategory":null,"ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":null,"EPubDate":"","PubModel":"","JCR":"Q4","JCRName":"Chemical Engineering","Score":null,"Total":0}
Enantioface-differentiating hydrogenation of the CO double bond using a modified Raney nickel: Role of the carboxylic acid added to the reaction system
A tartaric acid—sodium bromide—modified Raney nickel (TANaBrMRNi) is a unique catalyst for the enantioface-differentiating hydrogenation of 2-alkanones and β-ketoesters. The addition of carboxylic acid to the reaction system results in improvement of the optical yield over this catalyst. In this study, the enantioface-differentiating hydrogenations of 2-octanone and methyl acetoacetate were carried out to clarify how the added carboxylic acids improve the efficiency of the enantio-differentiation of the substrates over TANaBrMRNi. The participation of the conjugate bases and protons generated from the added carboxylic acid during the hydrogenation of 2-alkanones and β-ketoesters is proposed.
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