用吡咯、吲哚和丁二酰亚胺支架有机催化不对称合成 C-N 异构体。

IF 3.5 3区化学 Q2 CHEMISTRY, MULTIDISCIPLINARY

Chemistry - An Asian Journal Pub Date : 2024-11-10 DOI:10.1002/asia.202401132

Subhankar Biswas, Subham Kundu, Subhas Chandra Pan

{"title":"用吡咯、吲哚和丁二酰亚胺支架有机催化不对称合成 C-N 异构体。","authors":"Subhankar Biswas, Subham Kundu, Subhas Chandra Pan","doi":"10.1002/asia.202401132","DOIUrl":null,"url":null,"abstract":"An asymmetric synthesis of C-N atropisomers with pyrrole, oxindole and succinimide moities was developed via organocatalytic desymmetric Michael addition of 3-pyrrolyloxindole with prochiral N-aryl maleimides. The C-N atropisomers were obtained in acceptable yields with high diastero- and enantioselectivities (>20:1 dr, up to >99% ee). C-N Rotational energy barrier has also been determined.","PeriodicalId":145,"journal":{"name":"Chemistry - An Asian Journal","volume":" ","pages":"e202401132"},"PeriodicalIF":3.5000,"publicationDate":"2024-11-10","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":"0","resultStr":"{\"title\":\"Organocatalytic Asymmetric Synthesis of C-N Atropisomers with Pyrrole, Oxindole and Succinimide Scaffold.\",\"authors\":\"Subhankar Biswas, Subham Kundu, Subhas Chandra Pan\",\"doi\":\"10.1002/asia.202401132\",\"DOIUrl\":null,\"url\":null,\"abstract\":\"An asymmetric synthesis of C-N atropisomers with pyrrole, oxindole and succinimide moities was developed via organocatalytic desymmetric Michael addition of 3-pyrrolyloxindole with prochiral N-aryl maleimides. The C-N atropisomers were obtained in acceptable yields with high diastero- and enantioselectivities (>20:1 dr, up to >99% ee). C-N Rotational energy barrier has also been determined.\",\"PeriodicalId\":145,\"journal\":{\"name\":\"Chemistry - An Asian Journal\",\"volume\":\" \",\"pages\":\"e202401132\"},\"PeriodicalIF\":3.5000,\"publicationDate\":\"2024-11-10\",\"publicationTypes\":\"Journal Article\",\"fieldsOfStudy\":null,\"isOpenAccess\":false,\"openAccessPdf\":\"\",\"citationCount\":\"0\",\"resultStr\":null,\"platform\":\"Semanticscholar\",\"paperid\":null,\"PeriodicalName\":\"Chemistry - An Asian Journal\",\"FirstCategoryId\":\"1\",\"ListUrlMain\":\"https://doi.org/10.1002/asia.202401132\",\"RegionNum\":3,\"RegionCategory\":\"化学\",\"ArticlePicture\":[],\"TitleCN\":null,\"AbstractTextCN\":null,\"PMCID\":null,\"EPubDate\":\"\",\"PubModel\":\"\",\"JCR\":\"Q2\",\"JCRName\":\"CHEMISTRY, MULTIDISCIPLINARY\",\"Score\":null,\"Total\":0}","platform":"Semanticscholar","paperid":null,"PeriodicalName":"Chemistry - An Asian Journal","FirstCategoryId":"1","ListUrlMain":"https://doi.org/10.1002/asia.202401132","RegionNum":3,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":null,"EPubDate":"","PubModel":"","JCR":"Q2","JCRName":"CHEMISTRY, MULTIDISCIPLINARY","Score":null,"Total":0}

引用次数: 0

摘要

通过有机催化 3-吡咯并吲哚与亲手性 N-芳基马来酰亚胺的不对称迈克尔加成，开发了一种具有吡咯、吲哚和琥珀酰亚胺性质的 C-N 非对映异构体的不对称合成方法。以可接受的产率获得了 C-N 对映体，并具有很高的二主和对映选择性（>20:1 dr，ee>99%）。此外，还测定了 C-N 旋转能垒。

本文章由计算机程序翻译，如有差异，请以英文原文为准。

查看原文本刊更多论文

Organocatalytic Asymmetric Synthesis of C-N Atropisomers with Pyrrole, Oxindole and Succinimide Scaffold.

An asymmetric synthesis of C-N atropisomers with pyrrole, oxindole and succinimide moities was developed via organocatalytic desymmetric Michael addition of 3-pyrrolyloxindole with prochiral N-aryl maleimides. The C-N atropisomers were obtained in acceptable yields with high diastero- and enantioselectivities (>20:1 dr, up to >99% ee). C-N Rotational energy barrier has also been determined.

求助全文

通过发布文献求助，成功后即可免费获取论文全文。去求助

来源期刊

Chemistry - An Asian Journal 化学-化学综合

CiteScore

7.00

自引率

2.40%

发文量

535

审稿时长

1.3 months

期刊介绍： Chemistry—An Asian Journal is an international high-impact journal for chemistry in its broadest sense. The journal covers all aspects of chemistry from biochemistry through organic and inorganic chemistry to physical chemistry, including interdisciplinary topics. Chemistry—An Asian Journal publishes Full Papers, Communications, and Focus Reviews. A professional editorial team headed by Dr. Theresa Kueckmann and an Editorial Board (headed by Professor Susumu Kitagawa) ensure the highest quality of the peer-review process, the contents and the production of the journal. Chemistry—An Asian Journal is published on behalf of the Asian Chemical Editorial Society (ACES), an association of numerous Asian chemical societies, and supported by the Gesellschaft Deutscher Chemiker (GDCh, German Chemical Society), ChemPubSoc Europe, and the Federation of Asian Chemical Societies (FACS).