(3+2) Annulation of Donor–Acceptor Cyclopropanes with Difluoroenoxysilanes: Syntheses of gem-Difluorocyclopentenes via α,α-Difluoroketone Scaffolds

IF 3.6 2区 化学 Q1 CHEMISTRY, ORGANIC Journal of Organic Chemistry Pub Date : 2025-03-27 DOI:10.1021/acs.joc.4c03181
Neeraj Yadav, Prabal Banerjee
{"title":"(3+2) Annulation of Donor–Acceptor Cyclopropanes with Difluoroenoxysilanes: Syntheses of gem-Difluorocyclopentenes via α,α-Difluoroketone Scaffolds","authors":"Neeraj Yadav, Prabal Banerjee","doi":"10.1021/acs.joc.4c03181","DOIUrl":null,"url":null,"abstract":"Herein, we present an acid- and base-mediated approach for ring opening of donor–acceptor cyclopropanes (DACs) followed by (3+2) annulation, yielding biologically relevant <i>gem</i>-difluorinated cyclopentenes via α,α-difluoroketone scaffolds. Fluorinated rings are essential building blocks in drug discovery and materials research. This methodology has a broad substrate scope, is scalable, and provides a practical synthetic route to obtain value-added fluorinated compounds.","PeriodicalId":57,"journal":{"name":"Journal of Organic Chemistry","volume":"23 1","pages":""},"PeriodicalIF":3.6000,"publicationDate":"2025-03-27","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":"0","resultStr":null,"platform":"Semanticscholar","paperid":null,"PeriodicalName":"Journal of Organic Chemistry","FirstCategoryId":"1","ListUrlMain":"https://doi.org/10.1021/acs.joc.4c03181","RegionNum":2,"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

Herein, we present an acid- and base-mediated approach for ring opening of donor–acceptor cyclopropanes (DACs) followed by (3+2) annulation, yielding biologically relevant gem-difluorinated cyclopentenes via α,α-difluoroketone scaffolds. Fluorinated rings are essential building blocks in drug discovery and materials research. This methodology has a broad substrate scope, is scalable, and provides a practical synthetic route to obtain value-added fluorinated compounds.

Abstract Image

查看原文
分享 分享
微信好友 朋友圈 QQ好友 复制链接
本刊更多论文
(3+2)给受体环丙烷与二氟烯氧基硅烷的环化:通过α,α-二氟酮支架合成宝石-二氟环戊烯
在此,我们提出了一种酸和碱介导的方法,通过α,α-二氟酮支架打开供体-受体环丙烷(dac)的环,然后进行(3+2)环化,产生生物相关的宝石二氟化环戊烯。氟化环是药物发现和材料研究的重要组成部分。该方法具有广泛的底物范围,可扩展,并提供了一种实用的合成途径来获得增值氟化化合物。
本文章由计算机程序翻译,如有差异,请以英文原文为准。
求助全文
约1分钟内获得全文 去求助
来源期刊
Journal of Organic Chemistry
Journal of Organic Chemistry 化学-有机化学
CiteScore
6.20
自引率
11.10%
发文量
1467
审稿时长
2 months
期刊介绍: Journal of Organic Chemistry welcomes original contributions of fundamental research in all branches of the theory and practice of organic chemistry. In selecting manuscripts for publication, the editors place emphasis on the quality and novelty of the work, as well as the breadth of interest to the organic chemistry community.
期刊最新文献
Asymmetric Total Synthesis of Both C14 Epimers of Petromyzestrosterol Enables Stereochemical Assignment and Olfactory Activity Evaluation in Sea Lamprey. Antimicrobial Activities of Ophiobolins from Bipolaris maydis against Foodborne Pathogenic Bacteria via Biofilm Formation Inhibition. Electrochemical Intermolecular Benzylic C(sp3)-H Imidation via Bromide-Mediated Cross-Dehydrogenative Coupling. Structural Aspects of Proline Methanologues in Drug Design, Optimization, and Development. Unveiling the Potential of N-Hydroxyphthalimide with Zn in Alkylative Dearomatization of N-Alkylpyridinium Salts.
×
引用
GB/T 7714-2015
复制
MLA
复制
APA
复制
导出至
BibTeX EndNote RefMan NoteFirst NoteExpress
×
×
提示
您的信息不完整,为了账户安全,请先补充。
现在去补充
×
提示
您因"违规操作"
具体请查看互助需知
我知道了
×
提示
现在去查看 取消
×
提示
确定
0
微信
客服QQ
Book学术公众号 扫码关注我们
反馈
×
意见反馈
请填写您的意见或建议
请填写您的手机或邮箱
已复制链接
已复制链接
快去分享给好友吧!
我知道了
×
扫码分享
扫码分享
Book学术官方微信
Book学术文献互助
Book学术文献互助群
群 号:604180095
Book学术
文献互助 智能选刊 最新文献 互助须知 联系我们:info@booksci.cn
Book学术提供免费学术资源搜索服务,方便国内外学者检索中英文文献。致力于提供最便捷和优质的服务体验。
Copyright © 2023 Book学术 All rights reserved.
ghs 京公网安备 11010802042870号 京ICP备2023020795号-1