Chemodivergent synthesis of cis-4-hydroxyprolines from diastereomerically enriched epoxides†

IF 2.7 3区 化学 Q1 CHEMISTRY, ORGANIC Organic & Biomolecular Chemistry Pub Date : 2025-04-08 Epub Date: 2025-01-28 DOI:10.1039/d4ob01815j
Clement DaSilva , Grace Mauk , Lucas Forshee , Oliver Pope , Mathilde Doherty , Max Ongbongan , Nicholas Lutz , Zemirah Kamanya , Kara Chris Bhatt , Andrew Braham , Miranda Kubek , Summer Hawthorne , Gonzalo Campillo-Alvarado , Avik Bhattacharjee , Miriam A. Bowring , Robert V. O'Brien
{"title":"Chemodivergent synthesis of cis-4-hydroxyprolines from diastereomerically enriched epoxides†","authors":"Clement DaSilva ,&nbsp;Grace Mauk ,&nbsp;Lucas Forshee ,&nbsp;Oliver Pope ,&nbsp;Mathilde Doherty ,&nbsp;Max Ongbongan ,&nbsp;Nicholas Lutz ,&nbsp;Zemirah Kamanya ,&nbsp;Kara Chris Bhatt ,&nbsp;Andrew Braham ,&nbsp;Miranda Kubek ,&nbsp;Summer Hawthorne ,&nbsp;Gonzalo Campillo-Alvarado ,&nbsp;Avik Bhattacharjee ,&nbsp;Miriam A. Bowring ,&nbsp;Robert V. O'Brien","doi":"10.1039/d4ob01815j","DOIUrl":null,"url":null,"abstract":"<div><div>A method for synthesis of <em>cis</em>-4-hydroxyproline analogs is described. A <em>cis</em> epoxide is converted into a <em>cis</em>-4-hydroxyproline, while the <em>trans</em> epoxide is converted into a ketone or α-aminolactone in the presence of Lewis and Brønsted acids. We propose the divergent chemoselectivity is controlled by H-bonding within the <em>cis</em> epoxide.</div></div>","PeriodicalId":96,"journal":{"name":"Organic & Biomolecular Chemistry","volume":"23 19","pages":"Pages 4616-4621"},"PeriodicalIF":2.7000,"publicationDate":"2025-04-08","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":"0","resultStr":null,"platform":"Semanticscholar","paperid":null,"PeriodicalName":"Organic & Biomolecular Chemistry","FirstCategoryId":"92","ListUrlMain":"https://www.sciencedirect.com/org/science/article/pii/S1477052025003076","RegionNum":3,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":null,"EPubDate":"2025/1/28 0:00:00","PubModel":"Epub","JCR":"Q1","JCRName":"CHEMISTRY, ORGANIC","Score":null,"Total":0}
引用次数: 0

Abstract

A method for synthesis of cis-4-hydroxyproline analogs is described. A cis epoxide is converted into a cis-4-hydroxyproline, while the trans epoxide is converted into a ketone or α-aminolactone in the presence of Lewis and Brønsted acids. We propose the divergent chemoselectivity is controlled by H-bonding within the cis epoxide.
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
从非对映异构体富集环氧化物合成顺式-4-羟基脯氨酸的化学衍生物。
介绍了一种合成顺-4-羟基脯氨酸类似物的方法。顺式环氧化物在Lewis酸和Brønsted酸存在下转化为顺式-4-羟基脯氨酸,而反式环氧化物则转化为酮或α-氨基内酯。我们提出发散的化学选择性是由顺式环氧化物内部的氢键控制的。
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
Organic & Biomolecular Chemistry
Organic & Biomolecular Chemistry 化学-有机化学
CiteScore
5.50
自引率
9.40%
发文量
1056
审稿时长
1.3 months
期刊介绍: Organic & Biomolecular Chemistry is an international journal using integrated research in chemistry-organic chemistry. Founded in 2003 by the Royal Society of Chemistry, the journal is published in Semimonthly issues and has been indexed by SCIE, a leading international database. The journal focuses on the key research and cutting-edge progress in the field of chemistry-organic chemistry, publishes and reports the research results in this field in a timely manner, and is committed to becoming a window and platform for rapid academic exchanges among peers in this field. The journal's impact factor in 2023 is 2.9, and its CiteScore is 5.5.
期刊最新文献
Glycosyl modified nucleoside motifs for glycoconjugation of oligonucleotides. Dynamic N→B coordination and anion-selective turn-on fluorescence in oxadiazole-functionalized organoboranes. 3H-Phenothiazin-3-one: a photocatalyst for the mild oxidation of boronic acids under green LED irradiation. Correction: Cascade synthesis of 2,3-disubstituted quinazolinones from methyl anthranilates, isocyanides and arylboronic acids via NHC-palladium-catalyzed oxidative coupling reactions. Environmentally benign esterification and disproportionation using activation of acid anhydrides by molecular sieves 3A.
×
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