Jia-Qi Xie, Bing-Xia Wang, Ren-Xiao Liang and Yi-Xia Jia
{"title":"Copper-catalyzed asymmetric 1,2-arylboration of enamines: access to chiral borate-containing 3,3′-disubstituted isoindolinones†","authors":"Jia-Qi Xie, Bing-Xia Wang, Ren-Xiao Liang and Yi-Xia Jia","doi":"10.1039/D4OB00896K","DOIUrl":null,"url":null,"abstract":"<p >An enantioselective copper-catalyzed 1,2-arylboration reaction of enamines has been developed by employing (<em>R</em>)-xyl-BINAP as a chiral ligand. A number of chiral borate-containing 3,3′-disubstituted isoindolinones were obtained in moderate to good yields and good to excellent enantioselectivities from the reactions of <em>N</em>-(<em>o</em>-iodobenzoyl)enamines and bis(pinacolato)diboron (B<small><sub>2</sub></small>pin<small><sub>2</sub></small>) under mild reaction conditions. Synthetic transformations of the products were conducted to demonstrate the practicality of this reaction.</p>","PeriodicalId":96,"journal":{"name":"Organic & Biomolecular Chemistry","volume":null,"pages":null},"PeriodicalIF":2.9000,"publicationDate":"2024-07-03","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":"0","resultStr":null,"platform":"Semanticscholar","paperid":null,"PeriodicalName":"Organic & Biomolecular Chemistry","FirstCategoryId":"92","ListUrlMain":"https://pubs.rsc.org/en/content/articlelanding/2024/ob/d4ob00896k","RegionNum":3,"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
An enantioselective copper-catalyzed 1,2-arylboration reaction of enamines has been developed by employing (R)-xyl-BINAP as a chiral ligand. A number of chiral borate-containing 3,3′-disubstituted isoindolinones were obtained in moderate to good yields and good to excellent enantioselectivities from the reactions of N-(o-iodobenzoyl)enamines and bis(pinacolato)diboron (B2pin2) under mild reaction conditions. Synthetic transformations of the products were conducted to demonstrate the practicality of this reaction.