{"title":"溶剂诱导的吡咯酯铃木偶联区域选择性逆转","authors":"Yanan Zhang, S. Handy","doi":"10.2174/1874095200802010058","DOIUrl":null,"url":null,"abstract":"During a study of the regioselectivity of the Suzuki coupling of dihalopyrrole esters, the first instance of a re- versal of regioselectivity based upon a change in reaction solvent has been observed. It is believed that this change in re- gioselectivity is due to a change in solvation of the pyrrole ester, since a change in chemical shift values is observed for the C3 and C5 protons upon going from DMF to chloroform to 3:1 benzene/methanol. An attempted application of this regioselectivity to the synthesis of the lamellarin family of natural products is reported as well.","PeriodicalId":23020,"journal":{"name":"The Open Organic Chemistry Journal","volume":"37 1","pages":"58-64"},"PeriodicalIF":0.0000,"publicationDate":"2008-06-09","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":"6","resultStr":"{\"title\":\"A Solvent-Induced Reversal of Regioselectivity in the Suzuki Coupling of Pyrrole Esters\",\"authors\":\"Yanan Zhang, S. Handy\",\"doi\":\"10.2174/1874095200802010058\",\"DOIUrl\":null,\"url\":null,\"abstract\":\"During a study of the regioselectivity of the Suzuki coupling of dihalopyrrole esters, the first instance of a re- versal of regioselectivity based upon a change in reaction solvent has been observed. It is believed that this change in re- gioselectivity is due to a change in solvation of the pyrrole ester, since a change in chemical shift values is observed for the C3 and C5 protons upon going from DMF to chloroform to 3:1 benzene/methanol. An attempted application of this regioselectivity to the synthesis of the lamellarin family of natural products is reported as well.\",\"PeriodicalId\":23020,\"journal\":{\"name\":\"The Open Organic Chemistry Journal\",\"volume\":\"37 1\",\"pages\":\"58-64\"},\"PeriodicalIF\":0.0000,\"publicationDate\":\"2008-06-09\",\"publicationTypes\":\"Journal Article\",\"fieldsOfStudy\":null,\"isOpenAccess\":false,\"openAccessPdf\":\"\",\"citationCount\":\"6\",\"resultStr\":null,\"platform\":\"Semanticscholar\",\"paperid\":null,\"PeriodicalName\":\"The Open Organic Chemistry Journal\",\"FirstCategoryId\":\"1085\",\"ListUrlMain\":\"https://doi.org/10.2174/1874095200802010058\",\"RegionNum\":0,\"RegionCategory\":null,\"ArticlePicture\":[],\"TitleCN\":null,\"AbstractTextCN\":null,\"PMCID\":null,\"EPubDate\":\"\",\"PubModel\":\"\",\"JCR\":\"\",\"JCRName\":\"\",\"Score\":null,\"Total\":0}","platform":"Semanticscholar","paperid":null,"PeriodicalName":"The Open Organic Chemistry Journal","FirstCategoryId":"1085","ListUrlMain":"https://doi.org/10.2174/1874095200802010058","RegionNum":0,"RegionCategory":null,"ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":null,"EPubDate":"","PubModel":"","JCR":"","JCRName":"","Score":null,"Total":0}
A Solvent-Induced Reversal of Regioselectivity in the Suzuki Coupling of Pyrrole Esters
During a study of the regioselectivity of the Suzuki coupling of dihalopyrrole esters, the first instance of a re- versal of regioselectivity based upon a change in reaction solvent has been observed. It is believed that this change in re- gioselectivity is due to a change in solvation of the pyrrole ester, since a change in chemical shift values is observed for the C3 and C5 protons upon going from DMF to chloroform to 3:1 benzene/methanol. An attempted application of this regioselectivity to the synthesis of the lamellarin family of natural products is reported as well.
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