• 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

相似文献

1
Stereoselective Synthesis of trans-Olefins by the Copper-Mediated S(N)2' Reaction of Vinyl Oxazines with Grignard Reagents. Asymmetric Synthesis of D-threo-Sphingosines.通过乙烯基恶嗪与格氏试剂的铜介导S(N)2'反应立体选择性合成反式烯烃。D-苏型鞘氨醇的不对称合成。
Tetrahedron Lett. 2007;48(13):2345-2348. doi: 10.1016/j.tetlet.2007.01.145.
2
Reactions between Grignard reagents and heterocyclic N-oxides: stereoselective synthesis of substituted pyridines, piperidines, and piperazines.格氏试剂与杂环 N-氧化物的反应：取代吡啶、哌啶和哌嗪的立体选择性合成。
Org Biomol Chem. 2011 Jan 21;9(2):337-46. doi: 10.1039/c0ob00336k. Epub 2010 Nov 15.
3
Allylic functionalization of unactivated olefins with Grignard reagents.格氏试剂对未活化烯烃的烯丙基官能团化反应。
Angew Chem Int Ed Engl. 2014 Feb 3;53(6):1664-8. doi: 10.1002/anie.201309134. Epub 2014 Jan 23.
4
The reaction of Grignard reagents with Bunte salts: a thiol-free synthesis of sulfides.格氏试剂与 Bunte 盐的反应：一种无硫醇的硫化物合成方法。
Org Lett. 2014 Feb 21;16(4):1196-9. doi: 10.1021/ol500067f. Epub 2014 Feb 10.
5
S(N)2 ring opening of beta-lactones: an alternative to catalytic asymmetric conjugate additions.
J Org Chem. 2002 Jul 12;67(14):4680-3. doi: 10.1021/jo025519n.
6
Hetero-Diels-Alder reactions of alpha-aryl-beta-monohalo-alpha-nitrosoethylenes: diastereoselective synthesis of 6-substituted 3-aryl-4-halo-5,6-dihydro-4H-1,2-oxazines.α-芳基-β-单卤代-α-亚硝基乙烯的杂环狄尔斯-阿尔德反应：6-取代的3-芳基-4-卤代-5,6-二氢-4H-1,2-恶嗪的非对映选择性合成
J Org Chem. 2001 Nov 2;66(22):7334-41. doi: 10.1021/jo010476g.
7
Copper-catalyzed regioselective intramolecular oxidative α-functionalization of tertiary amines: an efficient synthesis of dihydro-1,3-oxazines.铜催化叔胺的区域选择性分子内氧化α-官能团化反应：二氢-1,3-恶嗪的高效合成
Angew Chem Int Ed Engl. 2013 Sep 9;52(37):9791-5. doi: 10.1002/anie.201304654. Epub 2013 Jul 24.
8
Highly regioselective copper-catalyzed cis- and trans-1-propenyl Grignard cleavage of hindered epoxides. application in propionate synthesis.高度区域选择性的铜催化受阻环氧化物的顺式和反式-1-丙烯基格氏试剂裂解。在丙酸盐合成中的应用。
J Org Chem. 2006 Jul 21;71(15):5826-9. doi: 10.1021/jo060833t.
9
One-Pot Synthesis of Trisubstituted Triazenes from Grignard Reagents and Organic Azides.一锅法由格氏试剂和有机叠氮化合物合成三取代三氮烯
Org Lett. 2018 Jun 1;20(11):3323-3326. doi: 10.1021/acs.orglett.8b01214. Epub 2018 May 14.
10
Iridium/Copper Co-catalyzed Anti-Stereoselective Ring Opening of Oxabenzonorbornadienes with Grignard Reagents.铱/铜共催化的 Grignard 试剂反非对映选择性开环氧杂双环[2.2.1]庚二烯。
J Org Chem. 2016 Sep 2;81(17):7817-23. doi: 10.1021/acs.joc.6b01479. Epub 2016 Aug 5.

引用本文的文献

1
Direct, intermolecular, enantioselective, iridium-catalyzed allylation of carbamates to form carbamate-protected, branched allylic amines.铱催化的氨基甲酸酯直接、分子间、对映选择性烯丙基化反应，用于形成氨基甲酸酯保护的支链烯丙基胺。
Org Lett. 2009 Jul 2;11(13):2944-7. doi: 10.1021/ol901151u.

本文引用的文献

1
Sphingolipids-Their Metabolic Pathways and the Pathobiochemistry of Neurodegenerative Diseases.鞘脂类——它们的代谢途径与神经退行性疾病的病理生物化学
Angew Chem Int Ed Engl. 1999 Jun 1;38(11):1532-1568. doi: 10.1002/(SICI)1521-3773(19990601)38:11<1532::AID-ANIE1532>3.0.CO;2-U.
2
An efficient synthesis of D-erythro- and D-threo-sphingosine from D-glucose: olefin cross-metathesis approach.一种从D-葡萄糖高效合成D-赤藓糖型和D-苏阿糖型鞘氨醇的方法：烯烃复分解法。
Org Lett. 2005 Dec 22;7(26):5805-7. doi: 10.1021/ol052320z.
3
Sphingolipid synthesis via olefin cross metathesis: preparation of a differentially protected building block and application to the synthesis of D-erythro-ceramide.通过烯烃复分解反应进行鞘脂合成：一种差异保护结构单元的制备及其在D-赤藓糖神经酰胺合成中的应用
Org Lett. 2004 Aug 19;6(17):2861-3. doi: 10.1021/ol049183a.
4
A practical synthesis of D-erythro-sphingosine using a cross-metathesis approach.一种使用交叉复分解方法对D-赤藓糖型鞘氨醇进行的实用合成。
Org Biomol Chem. 2004 Jun 7;2(11):1643-6. doi: 10.1039/b403568b. Epub 2004 Apr 20.
5
Multicomponent linchpin couplings. Reaction of dithiane anions with terminal epoxides, epichlorohydrin, and vinyl epoxides: efficient, rapid, and stereocontrolled assembly of advanced fragments for complex molecule synthesis.多组分关键偶联反应。二硫烷阴离子与末端环氧化物、环氧氯丙烷和乙烯基环氧化物的反应：用于复杂分子合成的高级片段的高效、快速且立体控制的组装。
J Am Chem Soc. 2003 Nov 26;125(47):14435-45. doi: 10.1021/ja0376238.
6
Hydrogen bond directed highly regioselective palladium-catalyzed allylic substitution.氢键导向的高度区域选择性钯催化烯丙基取代反应
J Am Chem Soc. 2003 Apr 30;125(17):5115-20. doi: 10.1021/ja028426w.
7
Aziridines: epoxides' ugly cousins?氮丙啶：环氧化物的难看近亲？
Chem Soc Rev. 2002 Sep;31(5):247-58. doi: 10.1039/b006015l.
8
Regio- and stereoselective synthesis of (E)-alkene trans-Xaa-Pro dipeptide mimetics utilizing organocopper-mediated anti-S(N)2' reactions.利用有机铜介导的反-S(N)2'反应实现（E）-烯烃反式-Xaa-Pro二肽模拟物的区域和立体选择性合成。
J Org Chem. 2002 Aug 23;67(17):6152-61. doi: 10.1021/jo025922u.
9
Diastereoselective synthesis of psi[(E)-CMe=CH]- and psi[(E)-CMe=CMe]- type dipeptide isosteres based on organocopper-mediated anti-S(N)2' reaction.
Org Lett. 2002 Apr 4;4(7):1055-8. doi: 10.1021/ol016835b.
10
Electronic effects on the regio- and enantioselectivity of the asymmetric aminohydroxylation of O-substituted 4-hydroxy-2-butenoates.电子对O-取代的4-羟基-2-丁烯酸酯不对称氨基羟基化反应的区域选择性和对映选择性的影响
Chirality. 2002 Feb-Mar;14(2-3):151-62. doi: 10.1002/chir.10050.

通过乙烯基恶嗪与格氏试剂的铜介导S(N)2'反应立体选择性合成反式烯烃。D-苏型鞘氨醇的不对称合成。

Stereoselective Synthesis of trans-Olefins by the Copper-Mediated S(N)2' Reaction of Vinyl Oxazines with Grignard Reagents. Asymmetric Synthesis of D-threo-Sphingosines.

作者信息

Singh Om V, Han Hyunsoo

机构信息

Department of Chemistry, The University of Texas at San Antonio, San Antonio, Texas 78249, USA.

出版信息

Tetrahedron Lett. 2007;48(13):2345-2348. doi: 10.1016/j.tetlet.2007.01.145.

DOI:10.1016/j.tetlet.2007.01.145
PMID:18958293
原文链接:https://pmc.ncbi.nlm.nih.gov/articles/PMC2572814/
Abstract

The S(N)2' reaction of 6-vinyl-5,6-dihydro-4H-[1,3]oxazines with Grignard reagents in the presence of CuCN was studied, and high trans selectivity for the formation of double bond was observed with a variety of RMgX. The S(N)2' reaction, coupled with regioselective asymmetric aminohydroxylation reaction, provided a highly efficient route for the asymmetric synthesis of D-threo-N-acetylsphingosine.

摘要

研究了6-乙烯基-5,6-二氢-4H-[1,3]恶嗪在CuCN存在下与格氏试剂的S(N)2'反应，观察到与多种RMgX反应时形成双键具有高反式选择性。S(N)2'反应与区域选择性不对称氨羟基化反应相结合，为D-苏式-N-乙酰鞘氨醇的不对称合成提供了一条高效路线。