{"title":"Phosphonamidates of Camphorsultam: Versatile Building Blocks for the Synthesis of P‐Chiral Phosphorous(V) Compounds","authors":"Yasutomo Yamamoto, Yurika Kambara, Ayase Matsumoto, Miku Murata, Mizuki Nakamoto, Tomoe Ishiura, Sakura Nakai, Hideyasu China, Kenji Watanabe, Akari Miyawaki, Junpei Matsuoka","doi":"10.1002/adsc.202401268","DOIUrl":null,"url":null,"abstract":"Camphorsultam was utilized for the optical resolution of <i>P</i>‐chiral phosphorous compounds. After chromatographic separation of diastereomeric <i>R</i><sub>P</sub>‐ and <i>S</i><sub>P</sub>‐ phosphonamidate intermediates, subsequent substitution reactions with phenol derivatives yielded <i>P</i>‐chiral phosphonic acid aryl esters with excellent enantioselectivities. In these processes, chiral sulfonamide of camphorsultam demonstrated superior abilities as an optical‐resolving agent and a good leaving group. This method was applied to the synthesis of <i>P</i>‐chiral phosphinic esters, phosphonamidates, and thiophosphonate diesters.","PeriodicalId":118,"journal":{"name":"Advanced Synthesis & Catalysis","volume":"35 1","pages":""},"PeriodicalIF":4.4000,"publicationDate":"2024-11-27","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":"0","resultStr":null,"platform":"Semanticscholar","paperid":null,"PeriodicalName":"Advanced Synthesis & Catalysis","FirstCategoryId":"92","ListUrlMain":"https://doi.org/10.1002/adsc.202401268","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
Camphorsultam was utilized for the optical resolution of <i>P</i>‐chiral phosphorous compounds. After chromatographic separation of diastereomeric <i>R</i><sub>P</sub>‐ and <i>S</i><sub>P</sub>‐ phosphonamidate intermediates, subsequent substitution reactions with phenol derivatives yielded <i>P</i>‐chiral phosphonic acid aryl esters with excellent enantioselectivities. In these processes, chiral sulfonamide of camphorsultam demonstrated superior abilities as an optical‐resolving agent and a good leaving group. This method was applied to the synthesis of <i>P</i>‐chiral phosphinic esters, phosphonamidates, and thiophosphonate diesters.
期刊介绍：
Advanced Synthesis & Catalysis (ASC) is the leading primary journal in organic, organometallic, and applied chemistry.
The high impact of ASC can be attributed to the unique focus of the journal, which publishes exciting new results from academic and industrial labs on efficient, practical, and environmentally friendly organic synthesis. While homogeneous, heterogeneous, organic, and enzyme catalysis are key technologies to achieve green synthesis, significant contributions to the same goal by synthesis design, reaction techniques, flow chemistry, and continuous processing, multiphase catalysis, green solvents, catalyst immobilization, and recycling, separation science, and process development are also featured in ASC. The Aims and Scope can be found in the Notice to Authors or on the first page of the table of contents in every issue.
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