Yiyin Liu , Kun Zhu , Xuemei Li , Xiaoyun Wu , Jinhui Feng , Atefeh Roosta , Qiaqing Wu , Dunming Zhu
{"title":"通过顺序光催化氧化-烷基化和酶还原实现烯烃的不对称羧羟化反应","authors":"Yiyin Liu , Kun Zhu , Xuemei Li , Xiaoyun Wu , Jinhui Feng , Atefeh Roosta , Qiaqing Wu , Dunming Zhu","doi":"10.1016/j.tchem.2024.100083","DOIUrl":null,"url":null,"abstract":"<div><p>Asymmetric carbohydroxylation of alkenes offers an efficient approach to access chiral alcohols, a class of versatile building blocks in pharmaceutical and agrochemical industries, from abundant simple alkenes. Herein we reported a sequential photo-biocatalysis protocol for the asymmetric carbohydroxylation of alkenes, involving a stepwise photocatalytic decarboxylative radical addition/Kornblum oxidation and enzymatic reduction. A series of chiral alcohols with bulky structures were synthesized in up to 75 % isolated yields and 99 % ee from <em>N-</em>hydroxyphthalimide esters and aryl alkenes.</p></div>","PeriodicalId":74918,"journal":{"name":"Tetrahedron chem","volume":"11 ","pages":"Article 100083"},"PeriodicalIF":0.0000,"publicationDate":"2024-07-04","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"https://www.sciencedirect.com/science/article/pii/S2666951X24000226/pdfft?md5=0a3f1b332418a2bdbabd201092a6755e&pid=1-s2.0-S2666951X24000226-main.pdf","citationCount":"0","resultStr":"{\"title\":\"Asymmetric carbohydroxylation of alkenes via sequential photocatalytic oxo-alkylation and enzymatic reduction\",\"authors\":\"Yiyin Liu , Kun Zhu , Xuemei Li , Xiaoyun Wu , Jinhui Feng , Atefeh Roosta , Qiaqing Wu , Dunming Zhu\",\"doi\":\"10.1016/j.tchem.2024.100083\",\"DOIUrl\":null,\"url\":null,\"abstract\":\"<div><p>Asymmetric carbohydroxylation of alkenes offers an efficient approach to access chiral alcohols, a class of versatile building blocks in pharmaceutical and agrochemical industries, from abundant simple alkenes. Herein we reported a sequential photo-biocatalysis protocol for the asymmetric carbohydroxylation of alkenes, involving a stepwise photocatalytic decarboxylative radical addition/Kornblum oxidation and enzymatic reduction. A series of chiral alcohols with bulky structures were synthesized in up to 75 % isolated yields and 99 % ee from <em>N-</em>hydroxyphthalimide esters and aryl alkenes.</p></div>\",\"PeriodicalId\":74918,\"journal\":{\"name\":\"Tetrahedron chem\",\"volume\":\"11 \",\"pages\":\"Article 100083\"},\"PeriodicalIF\":0.0000,\"publicationDate\":\"2024-07-04\",\"publicationTypes\":\"Journal Article\",\"fieldsOfStudy\":null,\"isOpenAccess\":false,\"openAccessPdf\":\"https://www.sciencedirect.com/science/article/pii/S2666951X24000226/pdfft?md5=0a3f1b332418a2bdbabd201092a6755e&pid=1-s2.0-S2666951X24000226-main.pdf\",\"citationCount\":\"0\",\"resultStr\":null,\"platform\":\"Semanticscholar\",\"paperid\":null,\"PeriodicalName\":\"Tetrahedron chem\",\"FirstCategoryId\":\"1085\",\"ListUrlMain\":\"https://www.sciencedirect.com/science/article/pii/S2666951X24000226\",\"RegionNum\":0,\"RegionCategory\":null,\"ArticlePicture\":[],\"TitleCN\":null,\"AbstractTextCN\":null,\"PMCID\":null,\"EPubDate\":\"\",\"PubModel\":\"\",\"JCR\":\"\",\"JCRName\":\"\",\"Score\":null,\"Total\":0}","platform":"Semanticscholar","paperid":null,"PeriodicalName":"Tetrahedron chem","FirstCategoryId":"1085","ListUrlMain":"https://www.sciencedirect.com/science/article/pii/S2666951X24000226","RegionNum":0,"RegionCategory":null,"ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":null,"EPubDate":"","PubModel":"","JCR":"","JCRName":"","Score":null,"Total":0}
Asymmetric carbohydroxylation of alkenes via sequential photocatalytic oxo-alkylation and enzymatic reduction
Asymmetric carbohydroxylation of alkenes offers an efficient approach to access chiral alcohols, a class of versatile building blocks in pharmaceutical and agrochemical industries, from abundant simple alkenes. Herein we reported a sequential photo-biocatalysis protocol for the asymmetric carbohydroxylation of alkenes, involving a stepwise photocatalytic decarboxylative radical addition/Kornblum oxidation and enzymatic reduction. A series of chiral alcohols with bulky structures were synthesized in up to 75 % isolated yields and 99 % ee from N-hydroxyphthalimide esters and aryl alkenes.