Stereocontrolled desymmetrization of 2,5-cyclohexadienones via organocatalytic domino sulfa-1,6-/1,4-addition or sulfa-1,6- /1,4-/sulfa-1,4-addition reactions
{"title":"Stereocontrolled desymmetrization of 2,5-cyclohexadienones via organocatalytic domino sulfa-1,6-/1,4-addition or sulfa-1,6- /1,4-/sulfa-1,4-addition reactions","authors":"Vanisha Sodhi, Deepak Sharma, Manisha Sharma, Pankaj Chauhan","doi":"10.1039/d4qo02097a","DOIUrl":null,"url":null,"abstract":"We have developed a desymmetrization of 2,5-cyclohexadienones tethered 3-cyano-4-styrylcoumarins via the amino-squaramide catalyzed initial regio-/enantio-selective sulfa-1,6-addition to the 3-cyano-4-styrylcoumarin moiety of the substrate, followed by an intramolecular vinylogous 1,4-addition to the dienone portion. An additional sulfa-Michael addition was observed when the thiols were taken in excess to create an additional stereogenic center. With our divergent approach, the two unique classes of hydrophenanthrene skeletons have been synthesized as single diastereoisomers in good to excellent yields and enantioselectivities (up to >99.5:0.5 er).","PeriodicalId":97,"journal":{"name":"Organic Chemistry Frontiers","volume":"336 1","pages":""},"PeriodicalIF":4.6000,"publicationDate":"2024-12-14","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":"0","resultStr":null,"platform":"Semanticscholar","paperid":null,"PeriodicalName":"Organic Chemistry Frontiers","FirstCategoryId":"92","ListUrlMain":"https://doi.org/10.1039/d4qo02097a","RegionNum":1,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":null,"EPubDate":"","PubModel":"","JCR":"Q1","JCRName":"CHEMISTRY, ORGANIC","Score":null,"Total":0}
引用次数: 0
Abstract
We have developed a desymmetrization of 2,5-cyclohexadienones tethered 3-cyano-4-styrylcoumarins via the amino-squaramide catalyzed initial regio-/enantio-selective sulfa-1,6-addition to the 3-cyano-4-styrylcoumarin moiety of the substrate, followed by an intramolecular vinylogous 1,4-addition to the dienone portion. An additional sulfa-Michael addition was observed when the thiols were taken in excess to create an additional stereogenic center. With our divergent approach, the two unique classes of hydrophenanthrene skeletons have been synthesized as single diastereoisomers in good to excellent yields and enantioselectivities (up to >99.5:0.5 er).
期刊介绍：
Organic Chemistry Frontiers is an esteemed journal that publishes high-quality research across the field of organic chemistry. It places a significant emphasis on studies that contribute substantially to the field by introducing new or significantly improved protocols and methodologies. The journal covers a wide array of topics which include, but are not limited to, organic synthesis, the development of synthetic methodologies, catalysis, natural products, functional organic materials, supramolecular and macromolecular chemistry, as well as physical and computational organic chemistry.
京公网安备 11010802042870号
京ICP备2023020795号-1
分享
求助内容：
应助结果提醒方式：
扫码关注我们
