{"title":"The Z-enoate Assisted Meyer-Schuster Rearrangement with Thiol Nucleophiles. An Approach for the Functionalized Vinyl Sulfides, and Sulfones.","authors":"Beeraiah Baire, Sumran Raikwar","doi":"10.1002/asia.202500080","DOIUrl":null,"url":null,"abstract":"<p><p>Vinyl sulfides and their sulfones act as very important building blocks in organic synthesis. Further they are prevalent in bioactive natural and unnatural products and exhibit diverse bioactivities. Here in we report a Z-enoate assisted Meyer-Schuster rearrangement approach for the rapid generation of 1,4-ketoester based vinyl sulfides. The thiols were employed as nucleophiles during this versatile transformation the propargylic alcohols. The process exhibited broader scope for thiols (aryl and alkyl), and propargylic alcohols. Further these vinyl sulfides were efficiently converted into the corresponding vinyl sulfones by employing a Mo-based oxidizing agent. Sodium borohydride reduction of the 1,4-ketoester based vinyl sulfides directly gave the butyrolactones having the vinyl sulfide unit. The phenols, alcohols and amines were found to be inefficient as nucleophiles to give the corresponding vinyl ethers.</p>","PeriodicalId":145,"journal":{"name":"Chemistry - An Asian Journal","volume":" ","pages":"e202500080"},"PeriodicalIF":3.5000,"publicationDate":"2025-03-07","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":"0","resultStr":null,"platform":"Semanticscholar","paperid":null,"PeriodicalName":"Chemistry - An Asian Journal","FirstCategoryId":"1","ListUrlMain":"https://doi.org/10.1002/asia.202500080","RegionNum":3,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":null,"EPubDate":"","PubModel":"","JCR":"Q2","JCRName":"CHEMISTRY, MULTIDISCIPLINARY","Score":null,"Total":0}
引用次数: 0
Abstract
Vinyl sulfides and their sulfones act as very important building blocks in organic synthesis. Further they are prevalent in bioactive natural and unnatural products and exhibit diverse bioactivities. Here in we report a Z-enoate assisted Meyer-Schuster rearrangement approach for the rapid generation of 1,4-ketoester based vinyl sulfides. The thiols were employed as nucleophiles during this versatile transformation the propargylic alcohols. The process exhibited broader scope for thiols (aryl and alkyl), and propargylic alcohols. Further these vinyl sulfides were efficiently converted into the corresponding vinyl sulfones by employing a Mo-based oxidizing agent. Sodium borohydride reduction of the 1,4-ketoester based vinyl sulfides directly gave the butyrolactones having the vinyl sulfide unit. The phenols, alcohols and amines were found to be inefficient as nucleophiles to give the corresponding vinyl ethers.
期刊介绍：
Chemistry—An Asian Journal is an international high-impact journal for chemistry in its broadest sense. The journal covers all aspects of chemistry from biochemistry through organic and inorganic chemistry to physical chemistry, including interdisciplinary topics.
Chemistry—An Asian Journal publishes Full Papers, Communications, and Focus Reviews.
A professional editorial team headed by Dr. Theresa Kueckmann and an Editorial Board (headed by Professor Susumu Kitagawa) ensure the highest quality of the peer-review process, the contents and the production of the journal.
Chemistry—An Asian Journal is published on behalf of the Asian Chemical Editorial Society (ACES), an association of numerous Asian chemical societies, and supported by the Gesellschaft Deutscher Chemiker (GDCh, German Chemical Society), ChemPubSoc Europe, and the Federation of Asian Chemical Societies (FACS).
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