{"title":"镍催化的酰基咪唑与丙烯醛或 β 酯烯酮的不对称迈克尔加成反应","authors":"Qian Shi, Jiani Sun, Jiangbo Wu, Xuehe Lu, Xiaoyu Wu","doi":"10.1002/cctc.202401324","DOIUrl":null,"url":null,"abstract":"An enantioselective Michael addition of α‐substituted acyl‐imidazoles to acrolein catalyzed by a nickel‐bisoxazoline complex has been developed. The use of strong Lewis acid TMSOTf as an additive to activate the Michael acceptors proved to be vital to the success of this process. This process tolerates a wide range of acyl‐imidazoles, and a series of conjugate adducts were obtained in high yields and good enantioselectivities. Besides acrolein, β‐ester ennones are also applicable in this process affording the corresponding conjugate adducts in high yields with good diastereoselectivities and enantioselectivites in most cases. The potential utility of the reaction system was confirmed through 2 mmol‐scale reaction and derivatization experiments.","PeriodicalId":141,"journal":{"name":"ChemCatChem","volume":"7 1","pages":""},"PeriodicalIF":3.8000,"publicationDate":"2024-09-10","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":"0","resultStr":"{\"title\":\"Nickel‐Catalyzed Asymmetric Michael Addition of Acyl Imidazoles to Acrolein or β‐Ester Enones\",\"authors\":\"Qian Shi, Jiani Sun, Jiangbo Wu, Xuehe Lu, Xiaoyu Wu\",\"doi\":\"10.1002/cctc.202401324\",\"DOIUrl\":null,\"url\":null,\"abstract\":\"An enantioselective Michael addition of α‐substituted acyl‐imidazoles to acrolein catalyzed by a nickel‐bisoxazoline complex has been developed. The use of strong Lewis acid TMSOTf as an additive to activate the Michael acceptors proved to be vital to the success of this process. This process tolerates a wide range of acyl‐imidazoles, and a series of conjugate adducts were obtained in high yields and good enantioselectivities. Besides acrolein, β‐ester ennones are also applicable in this process affording the corresponding conjugate adducts in high yields with good diastereoselectivities and enantioselectivites in most cases. The potential utility of the reaction system was confirmed through 2 mmol‐scale reaction and derivatization experiments.\",\"PeriodicalId\":141,\"journal\":{\"name\":\"ChemCatChem\",\"volume\":\"7 1\",\"pages\":\"\"},\"PeriodicalIF\":3.8000,\"publicationDate\":\"2024-09-10\",\"publicationTypes\":\"Journal Article\",\"fieldsOfStudy\":null,\"isOpenAccess\":false,\"openAccessPdf\":\"\",\"citationCount\":\"0\",\"resultStr\":null,\"platform\":\"Semanticscholar\",\"paperid\":null,\"PeriodicalName\":\"ChemCatChem\",\"FirstCategoryId\":\"92\",\"ListUrlMain\":\"https://doi.org/10.1002/cctc.202401324\",\"RegionNum\":3,\"RegionCategory\":\"化学\",\"ArticlePicture\":[],\"TitleCN\":null,\"AbstractTextCN\":null,\"PMCID\":null,\"EPubDate\":\"\",\"PubModel\":\"\",\"JCR\":\"Q2\",\"JCRName\":\"CHEMISTRY, PHYSICAL\",\"Score\":null,\"Total\":0}","platform":"Semanticscholar","paperid":null,"PeriodicalName":"ChemCatChem","FirstCategoryId":"92","ListUrlMain":"https://doi.org/10.1002/cctc.202401324","RegionNum":3,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":null,"EPubDate":"","PubModel":"","JCR":"Q2","JCRName":"CHEMISTRY, PHYSICAL","Score":null,"Total":0}
Nickel‐Catalyzed Asymmetric Michael Addition of Acyl Imidazoles to Acrolein or β‐Ester Enones
An enantioselective Michael addition of α‐substituted acyl‐imidazoles to acrolein catalyzed by a nickel‐bisoxazoline complex has been developed. The use of strong Lewis acid TMSOTf as an additive to activate the Michael acceptors proved to be vital to the success of this process. This process tolerates a wide range of acyl‐imidazoles, and a series of conjugate adducts were obtained in high yields and good enantioselectivities. Besides acrolein, β‐ester ennones are also applicable in this process affording the corresponding conjugate adducts in high yields with good diastereoselectivities and enantioselectivites in most cases. The potential utility of the reaction system was confirmed through 2 mmol‐scale reaction and derivatization experiments.
期刊介绍:
With an impact factor of 4.495 (2018), ChemCatChem is one of the premier journals in the field of catalysis. The journal provides primary research papers and critical secondary information on heterogeneous, homogeneous and bio- and nanocatalysis. The journal is well placed to strengthen cross-communication within between these communities. Its authors and readers come from academia, the chemical industry, and government laboratories across the world. It is published on behalf of Chemistry Europe, an association of 16 European chemical societies, and is supported by the German Catalysis Society.