Da-Qiu Cui, Gan-Lu Qian, Hui-Lin Zheng, Ye-Nan Yang, Cai-Ming Wang*, Bo Zhou, Xin Hong* and Long-Wu Ye*,
{"title":"Chiral Phosphoric Acid-Catalyzed Kinetic Resolution of Tertiary Alcohol-Tethered Ynamides via Controllable Hydroalkoxylation","authors":"Da-Qiu Cui, Gan-Lu Qian, Hui-Lin Zheng, Ye-Nan Yang, Cai-Ming Wang*, Bo Zhou, Xin Hong* and Long-Wu Ye*, ","doi":"10.1021/acscatal.4c0805510.1021/acscatal.4c08055","DOIUrl":null,"url":null,"abstract":"<p >Catalytic kinetic resolution has proven to be a powerful and practical method for the preparation of enantioenriched tertiary alcohols since their racemates are easy to access. However, this strategy is highly challenging and generally relies on transition-metal catalysis and is mostly limited to the construction of five- and six-membered O-heterocycles. Herein, we disclose an efficient and controllable kinetic resolution of tertiary alcohol-tethered ynamides enabled by chiral phosphoric acid catalysis, which represents a unique chiral Brønsted acid-catalyzed alkyne functionalization via kinetic resolution of tertiary alcohols. This metal-free protocol allows the practical and atom-economic formation of chiral medium-sized N-heterocycles such as nine-membered lactams and benzoxazepines with high enantioselectivities.</p>","PeriodicalId":9,"journal":{"name":"ACS Catalysis ","volume":"15 3","pages":"2424–2433 2424–2433"},"PeriodicalIF":13.1000,"publicationDate":"2025-01-27","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":"0","resultStr":null,"platform":"Semanticscholar","paperid":null,"PeriodicalName":"ACS Catalysis ","FirstCategoryId":"92","ListUrlMain":"https://pubs.acs.org/doi/10.1021/acscatal.4c08055","RegionNum":1,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":null,"EPubDate":"","PubModel":"","JCR":"Q1","JCRName":"CHEMISTRY, PHYSICAL","Score":null,"Total":0}
引用次数: 0
Abstract
Catalytic kinetic resolution has proven to be a powerful and practical method for the preparation of enantioenriched tertiary alcohols since their racemates are easy to access. However, this strategy is highly challenging and generally relies on transition-metal catalysis and is mostly limited to the construction of five- and six-membered O-heterocycles. Herein, we disclose an efficient and controllable kinetic resolution of tertiary alcohol-tethered ynamides enabled by chiral phosphoric acid catalysis, which represents a unique chiral Brønsted acid-catalyzed alkyne functionalization via kinetic resolution of tertiary alcohols. This metal-free protocol allows the practical and atom-economic formation of chiral medium-sized N-heterocycles such as nine-membered lactams and benzoxazepines with high enantioselectivities.
期刊介绍：
ACS Catalysis is an esteemed journal that publishes original research in the fields of heterogeneous catalysis, molecular catalysis, and biocatalysis. It offers broad coverage across diverse areas such as life sciences, organometallics and synthesis, photochemistry and electrochemistry, drug discovery and synthesis, materials science, environmental protection, polymer discovery and synthesis, and energy and fuels.
The scope of the journal is to showcase innovative work in various aspects of catalysis. This includes new reactions and novel synthetic approaches utilizing known catalysts, the discovery or modification of new catalysts, elucidation of catalytic mechanisms through cutting-edge investigations, practical enhancements of existing processes, as well as conceptual advances in the field. Contributions to ACS Catalysis can encompass both experimental and theoretical research focused on catalytic molecules, macromolecules, and materials that exhibit catalytic turnover.
求助内容：
应助结果提醒方式：
京公网安备 11010802042870号
