Controlling the position of the nucleophilic ring-opening of 2-EWG-substituted azetidinium salts with fluoride by the N-1-(1-naphthyl)ethyl substituent and BINAM-derived bis-urea organocatalyst

IF 2.1 3区 化学 Q2 CHEMISTRY, ORGANIC Tetrahedron Pub Date : 2024-09-14 DOI:10.1016/j.tet.2024.134274
Eiji Tayama , Ryoga Tsutsumi , Daisuke Uraguchi
{"title":"Controlling the position of the nucleophilic ring-opening of 2-EWG-substituted azetidinium salts with fluoride by the N-1-(1-naphthyl)ethyl substituent and BINAM-derived bis-urea organocatalyst","authors":"Eiji Tayama ,&nbsp;Ryoga Tsutsumi ,&nbsp;Daisuke Uraguchi","doi":"10.1016/j.tet.2024.134274","DOIUrl":null,"url":null,"abstract":"<div><p>BINAM (1,1′-binaphthyl-2,2′-diamine)-derived <em>bis</em>-urea-catalyzed nucleophilic ring-opening of optically active and diastereomerically pure 2-EWG (electron-withdrawing group)-substituted <em>N</em>-(1-(1-naphthyl)ethyl)azetidinium salts with cesium fluoride in dichloromethane at room temperature proceeds at the less sterically hindered 4-position over the electronically deficient 2-position. Selective ring-opening at the 4-position is achieved by the combination of chiral stereocenters, as in <em>N</em>-(1-(1-naphthyl)ethyl)azetidinium salt, and steric bulk of the chiral <em>bis</em>-urea catalysts. The reaction affords the corresponding γ-fluoro-α-aminobutyric acid derivatives in diastereomerically pure. This protocol is applicable to the synthesis of enantiomerically enriched (98 % ee) γ-fluoro-α-amino acid derivatives starting from the commercially available chiral 1-(1-naphthyl)ethylamine.</p></div>","PeriodicalId":437,"journal":{"name":"Tetrahedron","volume":null,"pages":null},"PeriodicalIF":2.1000,"publicationDate":"2024-09-14","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":"0","resultStr":null,"platform":"Semanticscholar","paperid":null,"PeriodicalName":"Tetrahedron","FirstCategoryId":"92","ListUrlMain":"https://www.sciencedirect.com/science/article/pii/S0040402024004551","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

BINAM (1,1′-binaphthyl-2,2′-diamine)-derived bis-urea-catalyzed nucleophilic ring-opening of optically active and diastereomerically pure 2-EWG (electron-withdrawing group)-substituted N-(1-(1-naphthyl)ethyl)azetidinium salts with cesium fluoride in dichloromethane at room temperature proceeds at the less sterically hindered 4-position over the electronically deficient 2-position. Selective ring-opening at the 4-position is achieved by the combination of chiral stereocenters, as in N-(1-(1-naphthyl)ethyl)azetidinium salt, and steric bulk of the chiral bis-urea catalysts. The reaction affords the corresponding γ-fluoro-α-aminobutyric acid derivatives in diastereomerically pure. This protocol is applicable to the synthesis of enantiomerically enriched (98 % ee) γ-fluoro-α-amino acid derivatives starting from the commercially available chiral 1-(1-naphthyl)ethylamine.

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
通过 N-1-(1-萘基)乙基取代基和 BINAM 衍生的双脲类有机催化剂控制 2-EWG 取代的氮杂环丁烷盐与氟化物发生亲核开环反应的位置
BINAM(1,1′-联萘-2、室温下,在二氯甲烷中用氟化铯催化具有光学活性和非对映纯度的 2-EWG(电子抽取基)取代的 N-(1-(1-萘基)乙基)氮杂环丁烷盐的双脲催化亲核开环反应,在立体阻碍较小的 4 位进行,而在电子缺陷较小的 2 位进行。通过结合手性立体中心(如 N-(1-(1-萘基)乙基)氮杂环丁烷盐)和手性双脲催化剂的立体体积,可实现 4 位的选择性开环。反应生成非对映纯的γ-氟-α-氨基丁酸衍生物。该方案适用于从市售的手性 1-(1-萘基)乙胺开始合成对映体富集(98 % ee)的γ-氟-α-氨基酸衍生物。
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
Tetrahedron
Tetrahedron 化学-有机化学
CiteScore
3.90
自引率
4.80%
发文量
439
审稿时长
34 days
期刊介绍: Tetrahedron publishes full accounts of research having outstanding significance in the broad field of organic chemistry and its related disciplines, such as organic materials and bio-organic chemistry. Regular papers in Tetrahedron are expected to represent detailed accounts of an original study having substantially greater scope and details than that found in a communication, as published in Tetrahedron Letters. Tetrahedron also publishes thematic collections of papers as special issues and ''Reports'', commissioned in-depth reviews providing a comprehensive overview of a research area.
期刊最新文献
Synthesis of 1,3,5-trisubstituted 1,2,4-triazoles enabled by a gold-catalyzed three-component reaction Transition-metal-free nucleophilic substitution of alkenyl boronic acids with propargylic mesylates sp3-carbon electrophiles Gold(III)-catalyzed regioselective synthesis of vinyl-substituted pyrazolo[1,4]-oxazepines via 7-exo-trig cyclization Recent progress in metal-catalyzed C(sp³)-P bond formation Transition metal promoted Brook rearrangement and its related reactions
×
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