{"title":"Access to Chiral α-Methyl-α-Aryl Carboxylic Acids via Phosphoric Acid-Catalyzed Kinetic Resolution of Biaryl Oxazepines","authors":"Guimei Dai, Yifei Ma, Weiwei Tan, Ting Tu, Bowen Zhu, Zhikang Wei, Liejin Zhou, Shi-Chao Ren, Xing Yang","doi":"10.1039/d5qo00953g","DOIUrl":null,"url":null,"abstract":"We disclose herein a chiral phosphoric acid-catalyzed kinetic resolution of racemic biaryl oxazepines with alcohols, giving a series of biaryl oxazepines and imidate products bearing a chiral center in good yields and enantioselectivities. The racemic biaryl oxazepine substrates could be readily synthesized from racemic carboxylic acids. Hydrolysis of the chiral imidate products afforded α-methyl-α-aryl carboxylic acids in high yields and enantioselectivities.","PeriodicalId":97,"journal":{"name":"Organic Chemistry Frontiers","volume":"29 1","pages":""},"PeriodicalIF":4.7000,"publicationDate":"2025-07-25","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":"0","resultStr":null,"platform":"Semanticscholar","paperid":null,"PeriodicalName":"Organic Chemistry Frontiers","FirstCategoryId":"92","ListUrlMain":"https://doi.org/10.1039/d5qo00953g","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
We disclose herein a chiral phosphoric acid-catalyzed kinetic resolution of racemic biaryl oxazepines with alcohols, giving a series of biaryl oxazepines and imidate products bearing a chiral center in good yields and enantioselectivities. The racemic biaryl oxazepine substrates could be readily synthesized from racemic carboxylic acids. Hydrolysis of the chiral imidate products afforded α-methyl-α-aryl carboxylic acids in high yields and enantioselectivities.
期刊介绍:
Organic Chemistry Frontiers is an esteemed journal that publishes high-quality research across the field of organic chemistry. It places a significant emphasis on studies that contribute substantially to the field by introducing new or significantly improved protocols and methodologies. The journal covers a wide array of topics which include, but are not limited to, organic synthesis, the development of synthetic methodologies, catalysis, natural products, functional organic materials, supramolecular and macromolecular chemistry, as well as physical and computational organic chemistry.