{"title":"三肽催化的 β-硝基苯炔与环己酮的不对称迈克尔加成反应","authors":"Kippei Maeda, Mitsuki Takeyama, Yoshihito Kohari, Miki Murata","doi":"10.1055/a-2307-0645","DOIUrl":null,"url":null,"abstract":"A tripeptide catalyst derived from natural L-amino acids was employed in the reaction of β-nitrostyrenes with cyclohexanone, serving as a model for the asymmetric Michael addition reaction. The reaction was conducted in the presence of H-Pro-Tle-Gly-OH and 2-Fluoro-4-ChloroBenzoic acid as co-catalysts (each at 20 mol%) in DMF-H2O (5:1) at 0℃ for 3 days. This process yielded the desired Michael adducts with excellent efficiency and good stereoselectivity (up to 98% yield, up to 92%ee).","PeriodicalId":509029,"journal":{"name":"Synlett","volume":"42 43","pages":""},"PeriodicalIF":0.0000,"publicationDate":"2024-04-15","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":"0","resultStr":"{\"title\":\"Tripeptide-Catalyzed Asymmetric Michael Addition Reaction of β-Nitrostyrenes with Cyclohexanone\",\"authors\":\"Kippei Maeda, Mitsuki Takeyama, Yoshihito Kohari, Miki Murata\",\"doi\":\"10.1055/a-2307-0645\",\"DOIUrl\":null,\"url\":null,\"abstract\":\"A tripeptide catalyst derived from natural L-amino acids was employed in the reaction of β-nitrostyrenes with cyclohexanone, serving as a model for the asymmetric Michael addition reaction. The reaction was conducted in the presence of H-Pro-Tle-Gly-OH and 2-Fluoro-4-ChloroBenzoic acid as co-catalysts (each at 20 mol%) in DMF-H2O (5:1) at 0℃ for 3 days. This process yielded the desired Michael adducts with excellent efficiency and good stereoselectivity (up to 98% yield, up to 92%ee).\",\"PeriodicalId\":509029,\"journal\":{\"name\":\"Synlett\",\"volume\":\"42 43\",\"pages\":\"\"},\"PeriodicalIF\":0.0000,\"publicationDate\":\"2024-04-15\",\"publicationTypes\":\"Journal Article\",\"fieldsOfStudy\":null,\"isOpenAccess\":false,\"openAccessPdf\":\"\",\"citationCount\":\"0\",\"resultStr\":null,\"platform\":\"Semanticscholar\",\"paperid\":null,\"PeriodicalName\":\"Synlett\",\"FirstCategoryId\":\"1085\",\"ListUrlMain\":\"https://doi.org/10.1055/a-2307-0645\",\"RegionNum\":0,\"RegionCategory\":null,\"ArticlePicture\":[],\"TitleCN\":null,\"AbstractTextCN\":null,\"PMCID\":null,\"EPubDate\":\"\",\"PubModel\":\"\",\"JCR\":\"\",\"JCRName\":\"\",\"Score\":null,\"Total\":0}","platform":"Semanticscholar","paperid":null,"PeriodicalName":"Synlett","FirstCategoryId":"1085","ListUrlMain":"https://doi.org/10.1055/a-2307-0645","RegionNum":0,"RegionCategory":null,"ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":null,"EPubDate":"","PubModel":"","JCR":"","JCRName":"","Score":null,"Total":0}
Tripeptide-Catalyzed Asymmetric Michael Addition Reaction of β-Nitrostyrenes with Cyclohexanone
A tripeptide catalyst derived from natural L-amino acids was employed in the reaction of β-nitrostyrenes with cyclohexanone, serving as a model for the asymmetric Michael addition reaction. The reaction was conducted in the presence of H-Pro-Tle-Gly-OH and 2-Fluoro-4-ChloroBenzoic acid as co-catalysts (each at 20 mol%) in DMF-H2O (5:1) at 0℃ for 3 days. This process yielded the desired Michael adducts with excellent efficiency and good stereoselectivity (up to 98% yield, up to 92%ee).
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