氧杂环丙二烯与α-吡喃酮的狄尔斯-阿尔德环加成反应。
Diels-Alder Cycloadditions of Oxacyclic Allenes and α-Pyrones.
作者信息
Wonilowicz Laura G, Mehta Milauni M, Kamecke Lisa L, French Sarah A, Garg Neil K
机构信息
Department of Chemistry and Biochemistry, University of California, Los Angeles, California 90095-1569, United States.
出版信息
Org Lett. 2024 Aug 2;26(30):6465-6470. doi: 10.1021/acs.orglett.4c02294. Epub 2024 Jul 24.
Abstract
Reactions of α-pyrones with oxacyclic allenes in Diels-Alder trappings are described. We investigate regioselectivity trends and perform competition experiments to assess the influence of structural and electronic features on relative reaction rates. We also demonstrate the stereospecific trapping of an oxacyclic allene, which proceeds in high optical yield. This study provides insight into strained cyclic allene reactivity, as well as new synthetic tools for the rapid construction of complex, heterocyclic scaffolds.
摘要
描述了α-吡喃酮与氧杂环丙二烯在狄尔斯-阿尔德捕获反应中的反应。我们研究区域选择性趋势，并进行竞争实验以评估结构和电子特征对相对反应速率的影响。我们还证明了氧杂环丙二烯的立体选择性捕获，其以高光学产率进行。这项研究深入了解了应变环状丙二烯的反应性，以及用于快速构建复杂杂环骨架的新合成工具。
相似文献
1
Diels-Alder Cycloadditions of Oxacyclic Allenes and α-Pyrones.氧杂环丙二烯与α-吡喃酮的狄尔斯-阿尔德环加成反应。
Org Lett. 2024 Aug 2;26(30):6465-6470. doi: 10.1021/acs.orglett.4c02294. Epub 2024 Jul 24.
2
Development of a Vinylated Cyclic Allene: A Fleeting Strained Diene for the Diels-Alder Reaction.乙烯基化环丙二烯的开发：一种用于狄尔斯-阿尔德反应的瞬态张力二烯。
Angew Chem Int Ed Engl. 2025 Aug 11;64(33):e202510319. doi: 10.1002/anie.202510319. Epub 2025 Jun 26.
3
Cycloadditions of Oxacyclic Allenes and a Catalytic Asymmetric Entryway to Enantioenriched Cyclic Allenes.环丙烯的环加成反应和手性催化进入方法合成对映富集的环丙烯。
Angew Chem Int Ed Engl. 2019 Apr 16;58(17):5653-5657. doi: 10.1002/anie.201900503. Epub 2019 Mar 20.
4
Systemic treatments for metastatic cutaneous melanoma.转移性皮肤黑色素瘤的全身治疗
Cochrane Database Syst Rev. 2018 Feb 6;2(2):CD011123. doi: 10.1002/14651858.CD011123.pub2.
5
Zigzag-Type Molecular Belts: Synthesis, Structure, and Properties.之字形分子带：合成、结构与性质
Acc Chem Res. 2025 Jul 2. doi: 10.1021/acs.accounts.5c00328.
6
Why Are Autistic People More Likely to Experience Suicidal Thoughts? Applying the Integrated Motivational-Volitional Model with Autistic Adults.为什么自闭症患者更容易产生自杀念头？将综合动机-意志模型应用于成年自闭症患者。
Autism Adulthood. 2024 Sep 16;6(3):272-283. doi: 10.1089/aut.2023.0039. eCollection 2024 Sep.
7
Diels-Alder cycloadditions of strained azacyclic allenes.张力杂环丙二烯的 Diels-Alder 环加成反应。
Nat Chem. 2018 Sep;10(9):953-960. doi: 10.1038/s41557-018-0080-1. Epub 2018 Jul 30.
8
Comparison of self-administered survey questionnaire responses collected using mobile apps versus other methods.使用移动应用程序与其他方法收集的自我管理调查问卷回复的比较。
Cochrane Database Syst Rev. 2015 Jul 27;2015(7):MR000042. doi: 10.1002/14651858.MR000042.pub2.
9
Reactivity of Anomalous Aziridines for Versatile Access to High Fsp Amine Chemical Space.异常氮丙啶对广泛进入高Fsp胺化学空间的反应活性。
Acc Chem Res. 2025 Jan 21;58(2):231-249. doi: 10.1021/acs.accounts.4c00670. Epub 2024 Dec 30.
本文引用的文献
1
Access to Complex Scaffolds Through [2 + 2] Cycloadditions of Strained Cyclic Allenes.通过张力环状丙二烯的[2 + 2]环加成反应制备复杂支架
J Am Chem Soc. 2024 Jun 5;146(22):15420-15427. doi: 10.1021/jacs.4c03369. Epub 2024 May 20.
2
Total Synthesis of Lissodendoric Acid A.利松烷酸 A 的全合成。
Angew Chem Int Ed Engl. 2024 Aug 5;63(32):e202406676. doi: 10.1002/anie.202406676. Epub 2024 Jul 3.
3
Cyclic Allene Approach to the Manzamine Alkaloid Keramaphidin B.环状丙二烯方法合成曼扎明生物碱凯拉马芬丁 B。
Org Lett. 2023 Aug 4;25(30):5553-5557. doi: 10.1021/acs.orglett.3c01489. Epub 2023 Jun 30.
4
Stereoselective Intramolecular [2+2] Trapping of 1,2-Cyclohexadienes: a Route to Rigid, Angularly Fused Tricyclic Scaffolds.1,2-环己二烯的立体选择性分子内[2+2]捕获：通向刚性、角稠合三环骨架的途径。
Chemistry. 2023 Sep 12;29(51):e202301668. doi: 10.1002/chem.202301668. Epub 2023 Aug 7.
5
Total synthesis of lissodendoric acid A via stereospecific trapping of a strained cyclic allene.通过立体选择性捕获应变环状丙二烯，全合成 lissodendoric 酸 A。
Science. 2023 Jan 20;379(6629):261-265. doi: 10.1126/science.ade0032. Epub 2023 Jan 19.
6
2 + 2 Trapping of Acyloxy-1,2-cyclohexadienes with Styrenes and Electron-Deficient Olefins.2+2 捕获酰氧基-1,2-环己二烯与苯乙烯和缺电子烯烃。
Org Lett. 2022 Dec 30;24(51):9497-9501. doi: 10.1021/acs.orglett.2c03978. Epub 2022 Dec 15.
7
Merging Metals and Strained Intermediates.金属与应变中间体的融合
Chem Catal. 2022 Aug 18;2(8):1870-1879. doi: 10.1016/j.checat.2022.06.014. Epub 2022 Jul 21.
8
Leveraging Fleeting Strained Intermediates to Access Complex Scaffolds.利用瞬态应变中间体构建复杂骨架。
JACS Au. 2021 Jul 26;1(7):897-912. doi: 10.1021/jacsau.1c00214. Epub 2021 Jun 23.
9
Palladium-Catalyzed Annulations of Strained Cyclic Allenes.钯催化的张力环丙二烯的环化反应。
J Am Chem Soc. 2021 Jun 30;143(25):9338-9342. doi: 10.1021/jacs.1c04896. Epub 2021 Jun 18.
10
Cycloaddition Cascades of Strained Alkynes and Oxadiazinones.环张力炔烃与恶二嗪酮的环加成串联反应
Angew Chem Int Ed Engl. 2021 Aug 9;60(33):18201-18208. doi: 10.1002/anie.202105244. Epub 2021 Jul 6.
Zotero 插件