{"title":"Contrasting Facial Selectivity of a Squaramide‐Tagged Proline in the Asymmetric Michael Addition of Ketones to Maleimides","authors":"Kiran Kumari , Akram Gulam Hussain Khan , Srinivasan Easwar","doi":"10.1002/adsc.202400791","DOIUrl":null,"url":null,"abstract":"<div><div>A squaramide moiety was introduced at the C‐4 position of proline to afford an organocatalyst that served as a stereocontrol element to promote the asymmetric Michael addition of cyclic ketones to maleimides. A variety of chiral succinimides were obtained by the conjugate addition in 84–98% yield accompanied by 58–96% enantioselectivity. The results also include an interesting contrast in the facial selectivity observed with cyclohexanones and cycloheptanones, whereas an asymmetric desymmetrization of 4‐alkyl cyclohexanones was also achieved using the transformation.</div></div>","PeriodicalId":118,"journal":{"name":"Advanced Synthesis & Catalysis","volume":"366 22","pages":"Pages 4715-4722"},"PeriodicalIF":4.4000,"publicationDate":"2024-11-19","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":"0","resultStr":null,"platform":"Semanticscholar","paperid":null,"PeriodicalName":"Advanced Synthesis & Catalysis","FirstCategoryId":"92","ListUrlMain":"https://www.sciencedirect.com/org/science/article/pii/S1615415024005211","RegionNum":2,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":null,"EPubDate":"","PubModel":"","JCR":"Q2","JCRName":"CHEMISTRY, APPLIED","Score":null,"Total":0}
引用次数: 0
Abstract
A squaramide moiety was introduced at the C‐4 position of proline to afford an organocatalyst that served as a stereocontrol element to promote the asymmetric Michael addition of cyclic ketones to maleimides. A variety of chiral succinimides were obtained by the conjugate addition in 84–98% yield accompanied by 58–96% enantioselectivity. The results also include an interesting contrast in the facial selectivity observed with cyclohexanones and cycloheptanones, whereas an asymmetric desymmetrization of 4‐alkyl cyclohexanones was also achieved using the transformation.
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Advanced Synthesis & Catalysis (ASC) is the leading primary journal in organic, organometallic, and applied chemistry.
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