{"title":"Synthesis of tetrahydropyrans via an intermolecular oxa-michael/michael stepwise cycloaddition","authors":"","doi":"10.1016/j.tetlet.2024.155215","DOIUrl":null,"url":null,"abstract":"<div><p>An intermolecular highly diastereoselective oxa-Michael/Michael type stepwise cycloaddition was developed to synthesize tetrahydropyrans, using an allylic alcohol obtained from Baylis-Hillman reaction and methyl 2-(4-nitrophenyl) acrylate. These molecules were obtained in low to good yields using DBU as a base at 70 °C. This methodology provides a convenient and atom-economical approach for accessing tetrahydropyrans bearing three stereogenic centers, expanding the synthetic applicability and versatility of the oxa-Michael reactions.</p></div>","PeriodicalId":438,"journal":{"name":"Tetrahedron Letters","volume":null,"pages":null},"PeriodicalIF":1.5000,"publicationDate":"2024-07-25","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"https://www.sciencedirect.com/science/article/pii/S0040403924003101/pdfft?md5=8f546eef90b5029ea7ca6ccf93c67ccc&pid=1-s2.0-S0040403924003101-main.pdf","citationCount":"0","resultStr":null,"platform":"Semanticscholar","paperid":null,"PeriodicalName":"Tetrahedron Letters","FirstCategoryId":"92","ListUrlMain":"https://www.sciencedirect.com/science/article/pii/S0040403924003101","RegionNum":4,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":null,"EPubDate":"","PubModel":"","JCR":"Q3","JCRName":"CHEMISTRY, ORGANIC","Score":null,"Total":0}
引用次数: 0
Abstract
An intermolecular highly diastereoselective oxa-Michael/Michael type stepwise cycloaddition was developed to synthesize tetrahydropyrans, using an allylic alcohol obtained from Baylis-Hillman reaction and methyl 2-(4-nitrophenyl) acrylate. These molecules were obtained in low to good yields using DBU as a base at 70 °C. This methodology provides a convenient and atom-economical approach for accessing tetrahydropyrans bearing three stereogenic centers, expanding the synthetic applicability and versatility of the oxa-Michael reactions.
期刊介绍:
Tetrahedron Letters provides maximum dissemination of outstanding developments in organic chemistry. The journal is published weekly and covers developments in techniques, structures, methods and conclusions in experimental and theoretical organic chemistry. Rapid publication of timely and significant research results enables researchers from all over the world to transmit quickly their new contributions to large, international audiences.