{"title":"nhc催化同烯酸酯反应对映选择性合成2-硝基四萘林衍生物","authors":"Aniruddh Pratap, Prof. Dr. Biswajit Maji","doi":"10.1002/ajoc.202500588","DOIUrl":null,"url":null,"abstract":"<p>We report herein a highly diastereo- and enantioselective homoenolate addition reaction to <i>E</i>-3-nitro-1,2-dihydronaphthalene via the NHC-bound azolium homoenolate pathway, affording 2-nitrotetralins in very good chemical yields. The key 2-nitrotetralin derivatives, featuring two adjoining stereocenters, exhibit structural resemblance to the serrulatane and amphilectane diterpene natural products and pharmaceutically relevant ingredients. This catalytic asymmetric process offers a broad substrate scope, accommodating a wide range of enals and nitroalkenes embedded in tetralin or chroman frameworks, thereby yielding 2-nitrotetralin and 3-nitrochroman derivatives with three contiguous stereocenters. Other important features include: (i) readily accessible nitroalkenes and enals, including commercially available NHC-catalyst; (ii) simplicity of the reaction conditions; and (iii) the formation of C<sub>3</sub>-nitro-containing tetralins and chroman cores with a high level of diastereo- and enantioselectivities (up to >99:1 dr and 95% ee), along with several powerful synthetic transformations and functionalizations.</p>","PeriodicalId":130,"journal":{"name":"Asian Journal of Organic Chemistry","volume":"14 9","pages":""},"PeriodicalIF":2.7000,"publicationDate":"2025-07-09","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":"0","resultStr":"{\"title\":\"Enantioselective Synthesis of 2-Nitrotetralin Derivatives via NHC-Catalyzed Homoenolate Reactions\",\"authors\":\"Aniruddh Pratap, Prof. Dr. Biswajit Maji\",\"doi\":\"10.1002/ajoc.202500588\",\"DOIUrl\":null,\"url\":null,\"abstract\":\"<p>We report herein a highly diastereo- and enantioselective homoenolate addition reaction to <i>E</i>-3-nitro-1,2-dihydronaphthalene via the NHC-bound azolium homoenolate pathway, affording 2-nitrotetralins in very good chemical yields. The key 2-nitrotetralin derivatives, featuring two adjoining stereocenters, exhibit structural resemblance to the serrulatane and amphilectane diterpene natural products and pharmaceutically relevant ingredients. This catalytic asymmetric process offers a broad substrate scope, accommodating a wide range of enals and nitroalkenes embedded in tetralin or chroman frameworks, thereby yielding 2-nitrotetralin and 3-nitrochroman derivatives with three contiguous stereocenters. Other important features include: (i) readily accessible nitroalkenes and enals, including commercially available NHC-catalyst; (ii) simplicity of the reaction conditions; and (iii) the formation of C<sub>3</sub>-nitro-containing tetralins and chroman cores with a high level of diastereo- and enantioselectivities (up to >99:1 dr and 95% ee), along with several powerful synthetic transformations and functionalizations.</p>\",\"PeriodicalId\":130,\"journal\":{\"name\":\"Asian Journal of Organic Chemistry\",\"volume\":\"14 9\",\"pages\":\"\"},\"PeriodicalIF\":2.7000,\"publicationDate\":\"2025-07-09\",\"publicationTypes\":\"Journal Article\",\"fieldsOfStudy\":null,\"isOpenAccess\":false,\"openAccessPdf\":\"\",\"citationCount\":\"0\",\"resultStr\":null,\"platform\":\"Semanticscholar\",\"paperid\":null,\"PeriodicalName\":\"Asian Journal of Organic Chemistry\",\"FirstCategoryId\":\"92\",\"ListUrlMain\":\"https://aces.onlinelibrary.wiley.com/doi/10.1002/ajoc.202500588\",\"RegionNum\":4,\"RegionCategory\":\"化学\",\"ArticlePicture\":[],\"TitleCN\":null,\"AbstractTextCN\":null,\"PMCID\":null,\"EPubDate\":\"\",\"PubModel\":\"\",\"JCR\":\"Q1\",\"JCRName\":\"CHEMISTRY, ORGANIC\",\"Score\":null,\"Total\":0}","platform":"Semanticscholar","paperid":null,"PeriodicalName":"Asian Journal of Organic Chemistry","FirstCategoryId":"92","ListUrlMain":"https://aces.onlinelibrary.wiley.com/doi/10.1002/ajoc.202500588","RegionNum":4,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":null,"EPubDate":"","PubModel":"","JCR":"Q1","JCRName":"CHEMISTRY, ORGANIC","Score":null,"Total":0}
Enantioselective Synthesis of 2-Nitrotetralin Derivatives via NHC-Catalyzed Homoenolate Reactions
We report herein a highly diastereo- and enantioselective homoenolate addition reaction to E-3-nitro-1,2-dihydronaphthalene via the NHC-bound azolium homoenolate pathway, affording 2-nitrotetralins in very good chemical yields. The key 2-nitrotetralin derivatives, featuring two adjoining stereocenters, exhibit structural resemblance to the serrulatane and amphilectane diterpene natural products and pharmaceutically relevant ingredients. This catalytic asymmetric process offers a broad substrate scope, accommodating a wide range of enals and nitroalkenes embedded in tetralin or chroman frameworks, thereby yielding 2-nitrotetralin and 3-nitrochroman derivatives with three contiguous stereocenters. Other important features include: (i) readily accessible nitroalkenes and enals, including commercially available NHC-catalyst; (ii) simplicity of the reaction conditions; and (iii) the formation of C3-nitro-containing tetralins and chroman cores with a high level of diastereo- and enantioselectivities (up to >99:1 dr and 95% ee), along with several powerful synthetic transformations and functionalizations.
期刊介绍:
Organic chemistry is the fundamental science that stands at the heart of chemistry, biology, and materials science. Research in these areas is vigorous and truly international, with three major regions making almost equal contributions: America, Europe and Asia. Asia now has its own top international organic chemistry journal—the Asian Journal of Organic Chemistry (AsianJOC)
The AsianJOC is designed to be a top-ranked international research journal and publishes primary research as well as critical secondary information from authors across the world. The journal covers organic chemistry in its entirety. Authors and readers come from academia, the chemical industry, and government laboratories.