Towards an asymmetric β-selective addition of azlactones to allenoates

IF 2.2 4区 化学 Q2 CHEMISTRY, ORGANIC Beilstein Journal of Organic Chemistry Pub Date : 2024-07-04 DOI:10.3762/bjoc.20.134
Behzad Nasiri, Ghaffar Pasdar, Paul Zebrowski, Katharina Röser, David Naderer, Mario Waser
{"title":"Towards an asymmetric β-selective addition of azlactones to allenoates","authors":"Behzad Nasiri, Ghaffar Pasdar, Paul Zebrowski, Katharina Röser, David Naderer, Mario Waser","doi":"10.3762/bjoc.20.134","DOIUrl":null,"url":null,"abstract":"<p><font size='+1'><b>Abstract</b></font></p>\n<p>We herein report the asymmetric organocatalytic addition of azlactones to allenoates. Upon using chiral quaternary ammonium salt catalysts, i.e., Maruoka&#8217;s binaphthyl-based spirocyclic ammonium salts, the addition of various azlactones to allenoates proceeds in a &#946;-selective manner with moderate levels of enantioselectivities (up to 83:17 er). Furthermore, the obtained products can be successfully engaged in nucleophilic ring opening reactions, thus giving highly functionalized &#945;-amino acid derivatives.</p>\n<p align='center'><img src='https://www.beilstein-journals.org/bjoc/content/figures/1860-5397-20-134-graphical-abstract.png?max-width=550' border='0'/></p>\n<p><i>Beilstein J. Org. Chem.</i> <b>2024,</b> <i>20,</i> 1504&#8211;1509.&#160;doi:10.3762/bjoc.20.134</p>","PeriodicalId":8756,"journal":{"name":"Beilstein Journal of Organic Chemistry","volume":null,"pages":null},"PeriodicalIF":2.2000,"publicationDate":"2024-07-04","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":"0","resultStr":null,"platform":"Semanticscholar","paperid":null,"PeriodicalName":"Beilstein Journal of Organic Chemistry","FirstCategoryId":"92","ListUrlMain":"https://doi.org/10.3762/bjoc.20.134","RegionNum":4,"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

We herein report the asymmetric organocatalytic addition of azlactones to allenoates. Upon using chiral quaternary ammonium salt catalysts, i.e., Maruoka’s binaphthyl-based spirocyclic ammonium salts, the addition of various azlactones to allenoates proceeds in a β-selective manner with moderate levels of enantioselectivities (up to 83:17 er). Furthermore, the obtained products can be successfully engaged in nucleophilic ring opening reactions, thus giving highly functionalized α-amino acid derivatives.

Abstract Image

Beilstein J. Org. Chem. 2024, 20, 1504–1509. doi:10.3762/bjoc.20.134

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
实现氮内酯与烯酸酯的不对称 β 选择性加成反应
摘要我们在此报告氮内酯与烯酸盐的不对称有机催化加成。在使用手性季铵盐催化剂(即 Maruoka’的二萘基螺环铵盐)时,各种氮内酯以中等水平的对映选择性(高达 83:17er)以β选择性的方式加成到烯酸盐。此外,得到的产物可以成功地参与亲核开环反应,从而得到高度官能化的 α-氨基酸衍生物。Chem.2024, 20, 1504–1509. doi:10.3762/bjoc.20.134
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
CiteScore
4.90
自引率
3.70%
发文量
167
审稿时长
1.4 months
期刊介绍: The Beilstein Journal of Organic Chemistry is an international, peer-reviewed, Open Access journal. It provides a unique platform for rapid publication without any charges (free for author and reader) – Platinum Open Access. The content is freely accessible 365 days a year to any user worldwide. Articles are available online immediately upon publication and are publicly archived in all major repositories. In addition, it provides a platform for publishing thematic issues (theme-based collections of articles) on topical issues in organic chemistry. The journal publishes high quality research and reviews in all areas of organic chemistry, including organic synthesis, organic reactions, natural product chemistry, structural investigations, supramolecular chemistry and chemical biology.
期刊最新文献
Access to optically active tetrafluoroethylenated amines based on [1,3]-proton shift reaction. Copper-catalyzed yne-allylic substitutions: concept and recent developments. Interaction of a pyrene derivative with cationic [60]fullerene in phospholipid membranes and its effects on photodynamic actions. Synthesis of spiroindolenines through a one-pot multistep process mediated by visible light. Young investigators in natural products chemistry, biosynthesis, and enzymology.
×
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:481959085
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