• 文献检索
  • 文档翻译
  • 深度研究
  • 学术资讯
  • Suppr Zotero 插件Zotero 插件
  • 邀请有礼
  • 套餐&价格
  • 历史记录
应用&插件
Suppr Zotero 插件Zotero 插件浏览器插件Mac 客户端Windows 客户端微信小程序
定价
高级版会员购买积分包购买API积分包
服务
文献检索文档翻译深度研究API 文档MCP 服务
关于我们
关于 Suppr公司介绍联系我们用户协议隐私条款
关注我们

Suppr 超能文献

核心技术专利:CN118964589B侵权必究
粤ICP备2023148730 号-1Suppr @ 2026

文献检索

告别复杂PubMed语法,用中文像聊天一样搜索,搜遍4000万医学文献。AI智能推荐,让科研检索更轻松。

立即免费搜索

文件翻译

保留排版,准确专业,支持PDF/Word/PPT等文件格式,支持 12+语言互译。

免费翻译文档

深度研究

AI帮你快速写综述,25分钟生成高质量综述,智能提取关键信息,辅助科研写作。

立即免费体验

用于合成3-取代苯酞的对映选择性野崎-日山-岸烯丙基化-内酯化反应

Enantioselective Nozaki-Hiyama-Kishi allylation-lactonization for the syntheses of 3-substituted phthalides.

作者信息

Kumbhar Sharad V, Chen Chinpiao

机构信息

Department of Chemistry, National Dong Hwa University Shoufeng Hualien 974 Taiwan

Department of Nursing, Tzu Chi University of Science and Technology Hualien 970 Taiwan.

出版信息

RSC Adv. 2018 Dec 12;8(72):41355-41357. doi: 10.1039/c8ra09575b. eCollection 2018 Dec 7.

DOI:10.1039/c8ra09575b
PMID:35559290
原文链接:https://pmc.ncbi.nlm.nih.gov/articles/PMC9091628/
Abstract

We report the synthesis of bipyridyl ligands and these ligands were applied in the chromium-catalyzed enantioselective Nozaki-Hiyama-Kishi allylation of substituted (2-ethoxycarbonyl)benzaldehydes and subsequently lactonized to synthesize phthalides with an optimal enantioselectivity of 99%. This approach was applied to synthesize ()-cytosporone E at a 71% yield in three steps.

摘要

我们报道了联吡啶配体的合成,并将这些配体应用于铬催化的取代(2-乙氧羰基)苯甲醛的对映选择性野崎-桧山-岸烯丙基化反应,随后进行内酯化反应以合成对映选择性最佳可达99%的苯酞。该方法被用于三步合成()-环孢菌素E,产率为71%。

相似文献

1
Enantioselective Nozaki-Hiyama-Kishi allylation-lactonization for the syntheses of 3-substituted phthalides.用于合成3-取代苯酞的对映选择性野崎-日山-岸烯丙基化-内酯化反应
RSC Adv. 2018 Dec 12;8(72):41355-41357. doi: 10.1039/c8ra09575b. eCollection 2018 Dec 7.
2
Synthesis of non-symmetric bis(oxazoline)-containing ligands and their application in the catalytic enantioselective Nozaki-Hiyama-Kishi allylation of benzaldehyde.含不对称双恶唑啉配体的合成及其在苯甲醛催化对映选择性野崎-桧山-岸烯丙基化反应中的应用。
Org Biomol Chem. 2008 Feb 7;6(3):562-6. doi: 10.1039/b715834c. Epub 2007 Dec 20.
3
The synthesis of a new class of chiral pincer ligands and their applications in enantioselective catalytic fluorinations and the Nozaki-Hiyama-Kishi reaction.一类新型手性钳状配体的合成及其在手性催化氟化反应和 Nozaki-Hiyama-Kishi 反应中的应用。
Chemistry. 2011 Dec 23;17(52):14922-8. doi: 10.1002/chem.201102375. Epub 2011 Nov 3.
4
Catalytic asymmetric Nozaki-Hiyama reactions with a tridentate bis(oxazolinyl)carbazole ligand.使用三齿双(恶唑啉基)咔唑配体的催化不对称野崎-桧山反应。
Chem Rec. 2008;8(3):169-81. doi: 10.1002/tcr.20148.
5
Catalytic enantioselective Nozaki-Hiyama allylation reaction with tethered bis(8-quinolinolato) (TBOx) chromium complex.使用 tethered 双(8-喹啉醇)(TBOx)铬配合物的催化对映选择性野崎-桧山烯丙基化反应。
J Am Chem Soc. 2006 Mar 1;128(8):2554-5. doi: 10.1021/ja058454p.
6
Chromium- and Metal-Reductant-Free Asymmetric Nozaki-Hiyama-Kishi (NHK) Reaction Enabled by Metallaphotoredox Catalysis.通过金属光氧化还原催化实现的无铬和无金属还原剂的不对称野崎-桧山-岸(NHK)反应
Angew Chem Int Ed Engl. 2024 Sep 9;63(37):e202408195. doi: 10.1002/anie.202408195. Epub 2024 Aug 8.
7
Asymmetric catalysis of Nozaki-Hiyama allylation and methallylation with a new tridentate bis(oxazolinyl)carbazole ligand.新型三齿双(恶唑啉基)咔唑配体对野崎-桧山烯丙基化反应和甲基烯丙基化反应的不对称催化作用
J Am Chem Soc. 2003 Feb 5;125(5):1140-1. doi: 10.1021/ja021243p.
8
The protecting-group directed diastereoselective Nozaki-Hiyama-Kishi (NHK) reaction: total synthesis and biological evaluation of zeaenol, 7-epi-zeaenol and its analogues.保护基导向的非对映选择性 Nozaki-Hiyama-Kishi(NHK)反应:泽烯醇、7-表泽烯醇及其类似物的全合成及生物评价。
Org Biomol Chem. 2014 Dec 21;12(47):9683-95. doi: 10.1039/c4ob01811g. Epub 2014 Oct 28.
9
Electrocatalytic Asymmetric Nozaki-Hiyama-Kishi Decarboxylative Coupling: Scope, Applications, and Mechanism.电催化不对称野崎-桧山-岸脱羧偶联反应:范围、应用及机理
J Am Chem Soc. 2024 Feb 21;146(7):4872-4882. doi: 10.1021/jacs.3c13442. Epub 2024 Feb 7.
10
Cobalt-Catalyzed Asymmetric Aza-Nozaki-Hiyama-Kishi (NHK) Reaction of α-Imino Esters with Alkenyl Halides.钴催化α-亚胺酯与卤代烯烃的不对称氮杂-野崎-桧山-岸(NHK)反应
Angew Chem Int Ed Engl. 2024 Feb 12;63(7):e202316012. doi: 10.1002/anie.202316012. Epub 2024 Jan 12.

引用本文的文献

1
Recent advancements in synthetic methodologies of 3-substituted phthalides and their application in the total synthesis of biologically active natural products.3-取代苯酞的合成方法学最新进展及其在生物活性天然产物全合成中的应用。
RSC Adv. 2020 Mar 27;10(21):12626-12652. doi: 10.1039/d0ra00701c. eCollection 2020 Mar 24.
2
Tautomerism and Self-Association in the Solution of New Pinene-Bipyridine and Pinene-Phenanthroline Derivatives.新松油烯-联吡啶和松油烯-菲咯啉衍生物在溶液中的互变异构和自组装。
Molecules. 2020 Jan 11;25(2):298. doi: 10.3390/molecules25020298.

本文引用的文献

1
Role of the Nozaki-Hiyama-Takai-Kishi Reaction in the Synthesis of Natural Products.诺泽斯基-反应、反应、反应在天然产物合成中的作用。
Chem Rev. 2017 Jun 28;117(12):8420-8446. doi: 10.1021/acs.chemrev.7b00144. Epub 2017 Jun 19.
2
Total Synthesis of Aquatolide: Wolff Ring Contraction and Late-Stage Nozaki-Hiyama-Kishi Medium-Ring Formation.水黄皮内酯的全合成:沃尔夫环收缩反应及后期的野崎-日山-岸田中环形成反应
Org Lett. 2016 Oct 21;18(20):5388-5391. doi: 10.1021/acs.orglett.6b02767. Epub 2016 Oct 5.
3
Concise synthesis of calystegines B2 and B3via intramolecular Nozaki-Hiyama-Kishi reaction.
通过分子内野崎-日山-岸反应简洁合成水苏碱B2和B3
Org Biomol Chem. 2016 Jun 7;14(21):4885-96. doi: 10.1039/c6ob00697c. Epub 2016 May 10.
4
Reactions of alkenylchromium reagents prepared from alkenyl trifluoromethanesulfonates (triflates) with chromium(II) chloride under nickel catalysis.在镍催化下,由烯基三氟甲磺酸酯(三氟甲磺酸盐)与氯化铬(II)制备的烯基铬试剂的反应。
J Am Chem Soc. 1986 Sep 1;108(19):6048-50. doi: 10.1021/ja00279a068.
5
Synthesis of non-symmetric bis(oxazoline)-containing ligands and their application in the catalytic enantioselective Nozaki-Hiyama-Kishi allylation of benzaldehyde.含不对称双恶唑啉配体的合成及其在苯甲醛催化对映选择性野崎-桧山-岸烯丙基化反应中的应用。
Org Biomol Chem. 2008 Feb 7;6(3):562-6. doi: 10.1039/b715834c. Epub 2007 Dec 20.
6
Design and synthesis of modular oxazoline ligands for the enantioselective chromium-catalyzed addition of allyl bromide to ketones.用于对映选择性铬催化溴化烯丙基加成到酮的模块化恶唑啉配体的设计与合成。
J Am Chem Soc. 2007 Mar 14;129(10):2752-3. doi: 10.1021/ja068915m. Epub 2007 Feb 20.
7
Catalytic enantioselective Nozaki-Hiyama allylation reaction with tethered bis(8-quinolinolato) (TBOx) chromium complex.使用 tethered 双(8-喹啉醇)(TBOx)铬配合物的催化对映选择性野崎-桧山烯丙基化反应。
J Am Chem Soc. 2006 Mar 1;128(8):2554-5. doi: 10.1021/ja058454p.
8
Stereochemical diversity in chiral ligand design: discovery and optimization of catalysts for the enantioselective addition of allylic halides to aldehydes.手性配体设计中的立体化学多样性:用于烯丙基卤化物对醛的对映选择性加成反应的催化剂的发现与优化
Org Lett. 2005 Apr 28;7(9):1837-9. doi: 10.1021/ol050528e.
9
Cytosporone E: racemic synthesis and preliminary antibacterial testing.环孢菌素E:外消旋体合成及初步抗菌测试。
Bioorg Med Chem. 2005 Feb 15;13(4):1409-13. doi: 10.1016/j.bmc.2004.10.018.
10
New catalytic cycle for couplings of aldehydes with organochromium reagents.醛与有机铬试剂偶联反应的新催化循环
Org Lett. 2004 Dec 23;6(26):5031-3. doi: 10.1021/ol047661b.