Palladium-Catalyzed Enantioselective Tandem Phosphinolation/Cyclization of ortho-Alkynylbenzaldehydes and H-Phosphine Oxides: Access to C1-Phosphinoylated 1H-Isochromenes
Linchun Zhang, Devendar Ponnam, Fan Yang, Meiqi Liang, Ruifeng Fan, Baomin Fan
{"title":"Palladium-Catalyzed Enantioselective Tandem Phosphinolation/Cyclization of ortho-Alkynylbenzaldehydes and H-Phosphine Oxides: Access to C1-Phosphinoylated 1H-Isochromenes","authors":"Linchun Zhang, Devendar Ponnam, Fan Yang, Meiqi Liang, Ruifeng Fan, Baomin Fan","doi":"10.1021/acs.orglett.5c00757","DOIUrl":null,"url":null,"abstract":"A novel and effective method for the synthesis of chiral C1-phosphinoylated 1<i>H</i>-isochromenes has been developed. The reaction proceeds via a tandem asymmetric addition/cyclization under a catalytic system of Pd(OAc)<sub>2</sub>, a Josiphos-based ligand <b>L9</b>, and ZnCl<sub>2</sub> in MeCN at 70 °C. This method demonstrates a broad substrate scope (27 examples), delivering excellent yields (up to 92%) and enantioselectivities (up to 95%).","PeriodicalId":54,"journal":{"name":"Organic Letters","volume":"8 1","pages":""},"PeriodicalIF":4.9000,"publicationDate":"2025-03-22","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":"0","resultStr":null,"platform":"Semanticscholar","paperid":null,"PeriodicalName":"Organic Letters","FirstCategoryId":"92","ListUrlMain":"https://doi.org/10.1021/acs.orglett.5c00757","RegionNum":1,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":null,"EPubDate":"","PubModel":"","JCR":"Q1","JCRName":"CHEMISTRY, ORGANIC","Score":null,"Total":0}
引用次数: 0
Abstract
A novel and effective method for the synthesis of chiral C1-phosphinoylated 1H-isochromenes has been developed. The reaction proceeds via a tandem asymmetric addition/cyclization under a catalytic system of Pd(OAc)2, a Josiphos-based ligand L9, and ZnCl2 in MeCN at 70 °C. This method demonstrates a broad substrate scope (27 examples), delivering excellent yields (up to 92%) and enantioselectivities (up to 95%).
期刊介绍：
Organic Letters invites original reports of fundamental research in all branches of the theory and practice of organic, physical organic, organometallic,medicinal, and bioorganic chemistry. Organic Letters provides rapid disclosure of the key elements of significant studies that are of interest to a large portion of the organic community. In selecting manuscripts for publication, the Editors place emphasis on the originality, quality and wide interest of the work. Authors should provide enough background information to place the new disclosure in context and to justify the rapid publication format. Back-to-back Letters will be considered. Full details should be reserved for an Article, which should appear in due course.
京公网安备 11010802042870号
京ICP备2023020795号-1
分享
求助内容：
应助结果提醒方式：
扫码关注我们
