{"title":"Organocatalytic Asymmetric Desymmetrization of Cyclopentene-1,3-diones via Formal Diaza-ene Reaction with Donor–Acceptor Hydrazones","authors":"Subhankar Biswas, Subhas Chandra Pan","doi":"10.1039/d5qo00081e","DOIUrl":null,"url":null,"abstract":"Herein we disclose a catalytic asymmetric desymmetrization of cyclopentene-1,3-diones via formal diaza-ene reaction/tautomerization with donor-acceptor hydrazones. H8-TRIP catalyst was found to be effective for this reaction. The chiral cyclopentane 1,3-diones embedded with hydrazone motif were obtained in good to high yields with excellent diastereo- and good to high enantioselectivities. The scope of the reaction was broad and few applications including a pyrazole formation reaction have been demonstrated.","PeriodicalId":97,"journal":{"name":"Organic Chemistry Frontiers","volume":"65 1","pages":""},"PeriodicalIF":4.6000,"publicationDate":"2025-02-19","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/d5qo00081e","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
Herein we disclose a catalytic asymmetric desymmetrization of cyclopentene-1,3-diones via formal diaza-ene reaction/tautomerization with donor-acceptor hydrazones. H8-TRIP catalyst was found to be effective for this reaction. The chiral cyclopentane 1,3-diones embedded with hydrazone motif were obtained in good to high yields with excellent diastereo- and good to high enantioselectivities. The scope of the reaction was broad and few applications including a pyrazole formation reaction have been demonstrated.
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.
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