Asymmetric Organocatalytic Synthesis of Chiral Polycyclic 1,4‐Dihydropyridines and Axially Chiral 4‐Arylpyridines Using 2,3‐Dioxopyrrolidines and 1,3‐Diketones
Cheng-Yu Ou, Bo-Wei Huang, Ting-Hung Chu, Po-Heng Lin, Jeng-Liang Han
{"title":"Asymmetric Organocatalytic Synthesis of Chiral Polycyclic 1,4‐Dihydropyridines and Axially Chiral 4‐Arylpyridines Using 2,3‐Dioxopyrrolidines and 1,3‐Diketones","authors":"Cheng-Yu Ou, Bo-Wei Huang, Ting-Hung Chu, Po-Heng Lin, Jeng-Liang Han","doi":"10.1002/ejoc.202500205","DOIUrl":null,"url":null,"abstract":"An asymmetric Michael/hemiketalization/amination process of 1,3‐diketones with 2,3‐dioxopyrrolidines catalysed by a quinine‐derived urea catalyst has been developed, which furnished a series of chiral polycyclic 1,4‐dihydropyridines in satisfactory yields and enantioselectivities (35‐94% yields for 2 steps and up to 99% ee). Moreover, the subsequent oxidative aromatization of chiral 1,4‐dihydropyridines delivers the chiral atropisomeric 4‐arylpyridines in 69‐94% yields and up to 95% ee.","PeriodicalId":167,"journal":{"name":"European Journal of Organic Chemistry","volume":"49 1","pages":""},"PeriodicalIF":2.5000,"publicationDate":"2025-03-21","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":"0","resultStr":null,"platform":"Semanticscholar","paperid":null,"PeriodicalName":"European Journal of Organic Chemistry","FirstCategoryId":"92","ListUrlMain":"https://doi.org/10.1002/ejoc.202500205","RegionNum":3,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":null,"EPubDate":"","PubModel":"","JCR":"Q2","JCRName":"CHEMISTRY, ORGANIC","Score":null,"Total":0}
引用次数: 0
Abstract
An asymmetric Michael/hemiketalization/amination process of 1,3‐diketones with 2,3‐dioxopyrrolidines catalysed by a quinine‐derived urea catalyst has been developed, which furnished a series of chiral polycyclic 1,4‐dihydropyridines in satisfactory yields and enantioselectivities (35‐94% yields for 2 steps and up to 99% ee). Moreover, the subsequent oxidative aromatization of chiral 1,4‐dihydropyridines delivers the chiral atropisomeric 4‐arylpyridines in 69‐94% yields and up to 95% ee.
期刊介绍：
The European Journal of Organic Chemistry (2019 ISI Impact Factor 2.889) publishes Full Papers, Communications, and Minireviews from the entire spectrum of synthetic organic, bioorganic and physical-organic chemistry. It is published on behalf of Chemistry Europe, an association of 16 European chemical societies.
The following journals have been merged to form two leading journals, the European Journal of Organic Chemistry and the European Journal of Inorganic Chemistry:
Liebigs Annalen
Bulletin des Sociétés Chimiques Belges
Bulletin de la Société Chimique de France
Gazzetta Chimica Italiana
Recueil des Travaux Chimiques des Pays-Bas
Anales de Química
Chimika Chronika
Revista Portuguesa de Química
ACH—Models in Chemistry
Polish Journal of Chemistry.
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
