• 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

通过螺硼酸酯催化肟醚的硼烷还原反应实现伯胺的不对称合成。

Asymmetric synthesis of primary amines via the spiroborate-catalyzed borane reduction of oxime ethers.

作者信息

Huang Xiaogen, Ortiz-Marciales Margarita, Huang Kun, Stepanenko Viatcheslav, Merced Francisco G, Ayala Angel M, Correa Wildeliz, Jesús Melvin De

机构信息

Department of Chemistry, University of Puerto Rico-Humacao, CUH Station, Humacao, Puerto Rico 00791.

出版信息

Org Lett. 2007 Apr 26;9(9):1793-5. doi: 10.1021/ol0704791. Epub 2007 Mar 31.

DOI:10.1021/ol0704791
PMID:17397177
原文链接:https://pmc.ncbi.nlm.nih.gov/articles/PMC2571073/
Abstract

[reaction: see text] The enantioselective borane reduction of O-benzyloxime ethers to primary amines was studied under catalytic conditions using the spiroborate esters 5-10 derived from nonracemic 1,2-amino alcohols and ethylene glycol. Effective catalytic conditions were achieved using only 10% of catalyst 5 derived from diphenylvalinol in dioxane at 0 degrees C resulting in complete conversion to the corresponding primary amine in up to 99% ee.

摘要

[反应：见正文] 在催化条件下，使用由非外消旋1,2-氨基醇和乙二醇衍生的螺硼酸酯5-10，研究了O-苄基肟醚对伯胺的对映选择性硼烷还原反应。在0℃下，在二氧六环中仅使用10%由二苯基缬氨醇衍生的催化剂5，就实现了有效的催化条件，从而以高达99%的对映体过量完全转化为相应的伯胺。

相似文献

1
Asymmetric synthesis of primary amines via the spiroborate-catalyzed borane reduction of oxime ethers.通过螺硼酸酯催化肟醚的硼烷还原反应实现伯胺的不对称合成。
Org Lett. 2007 Apr 26;9(9):1793-5. doi: 10.1021/ol0704791. Epub 2007 Mar 31.
2
Asymmetric synthesis of nonracemic primary amines via spiroborate-catalyzed reduction of pure (E)- and (Z)-O-benzyloximes: applications toward the synthesis of calcimimetic agents.通过螺环硼酸盐催化的纯 (E)-和 (Z)-O-苄氧基亚硝酮的还原对非外消旋伯胺的不对称合成：在钙敏感受体激动剂合成中的应用。
J Org Chem. 2013 Jun 7;78(11):5314-27. doi: 10.1021/jo400371x. Epub 2013 May 13.
3
Highly enantioselective borane reduction of heteroaryl and heterocyclic ketoxime ethers catalyzed by novel spiroborate ester derived from diphenylvalinol: application to the synthesis of nicotine analogues.由二苯基缬氨醇衍生的新型螺硼酸酯催化的杂芳基和杂环酮肟醚的高对映选择性硼烷还原反应：在尼古丁类似物合成中的应用
J Org Chem. 2008 Jun 6;73(11):4017-26. doi: 10.1021/jo800204n. Epub 2008 May 1.
4
Chiral epoxides via borane reduction of 2-haloketones catalyzed by spiroborate ester: application to the synthesis of optically pure 1,2-hydroxy ethers and 1,2-azido alcohols.手性环氧化物通过螺环硼酸酯酯催化的 2-卤代酮的硼烷还原：在光学纯 1,2-羟基醚和 1,2-叠氮醇合成中的应用。
J Org Chem. 2011 Mar 18;76(6):1883-6. doi: 10.1021/jo102294j. Epub 2011 Feb 4.
5
Spiroborate ester-mediated asymmetric synthesis of beta-hydroxy ethers and its conversion to highly enantiopure beta-amino ethers.螺硼酸酯介导的β-羟基醚的不对称合成及其向高对映体纯的β-氨基醚的转化。
J Org Chem. 2009 Jun 5;74(11):4195-202. doi: 10.1021/jo900666r.
6
Asymmetric synthesis of novel (1H-benzo[d]imidazol -2-ylthio)- and (di-n-butylamino-2-ylthio)acetamides.新型（1H-苯并[d]咪唑-2-基硫代）-和（二正丁基氨基-2-基硫代）乙酰胺的不对称合成。
Acta Pol Pharm. 2013 Mar-Apr;70(2):237-44.
7
Umpolung reactivity of difluoroenol silyl ethers with amines and amino alcohols. application to the synthesis of enantiopure alpha-difluoromethyl amines and amino acids.二氟烯醇硅醚与胺类及氨基醇的极性翻转反应性。用于对映体纯α-二氟甲基胺和氨基酸的合成。
J Org Chem. 2008 Apr 4;73(7):2564-9. doi: 10.1021/jo702328v. Epub 2008 Mar 11.
8
Rhodium-catalyzed enantioselective hydrogenation of oxime acetates.铑催化的肟乙酸酯的对映选择性氢化。
Org Lett. 2013 Feb 1;15(3):484-7. doi: 10.1021/ol303282u. Epub 2013 Jan 22.
9
Facile rearrangement of O-silylated oximes on reduction with boron trifluoride/borane.用三氟化硼/硼烷还原时，O-硅烷基化肟的简便重排反应。
J Org Chem. 2005 Nov 25;70(24):10132-4. doi: 10.1021/jo0516178.
10
Highly enantioselective Rh-catalyzed alkenylation of imines: synthesis of chiral allylic amines via asymmetric addition of potassium alkenyltrifluoroborates to N-tosyl imines.高对映选择性铑催化亚胺的烯基化反应：通过不对称加成钾烯基三氟硼酸盐到 N-对甲苯磺酰亚胺来合成手性烯丙基胺。
Org Lett. 2014 Jan 17;16(2):632-5. doi: 10.1021/ol4035897. Epub 2013 Dec 30.

引用本文的文献

1
Direct Electrosynthesis of an Amino Acid from a Biomass Derivative.从生物质衍生物直接电合成氨基酸。
ACS Electrochem. 2025 Mar 14;1(5):699-708. doi: 10.1021/acselectrochem.4c00171. eCollection 2025 May 1.
2
Nickel-catalysed asymmetric hydrogenation of oximes.镍催化的肟的不对称氢化。
Nat Chem. 2022 Aug;14(8):920-927. doi: 10.1038/s41557-022-00971-8. Epub 2022 Jun 13.
3
Simple ruthenium-catalyzed reductive amination enables the synthesis of a broad range of primary amines.简单的钌催化还原胺化反应能够实现广泛的伯胺的合成。

本文引用的文献

1
Asymmetric reduction of oxime ethers promoted by chiral spiroborate esters with an O3BN framework.具有O3BN骨架的手性螺硼酸酯促进肟醚的不对称还原反应。
J Org Chem. 2006 May 12;71(10):3998-4001. doi: 10.1021/jo060123n.
2
Enantioselective nitrile anion cyclization to substituted pyrrolidines. A highly efficient synthesis of (3S,4R)-N-tert-butyl-4-arylpyrrolidine-3-carboxylic acid.对映选择性腈阴离子环化反应合成取代吡咯烷。(3S,4R)-N-叔丁基-4-芳基吡咯烷-3-羧酸的高效合成。
J Org Chem. 2005 Apr 29;70(9):3592-601. doi: 10.1021/jo050178+.
3
Enantioselective reduction of oxime ethers with borane catalyzed by polymer-supported 2-piperazinemethanol.
Nat Commun. 2018 Oct 8;9(1):4123. doi: 10.1038/s41467-018-06416-6.
4
Asymmetric synthesis of nonracemic primary amines via spiroborate-catalyzed reduction of pure (E)- and (Z)-O-benzyloximes: applications toward the synthesis of calcimimetic agents.通过螺环硼酸盐催化的纯 (E)-和 (Z)-O-苄氧基亚硝酮的还原对非外消旋伯胺的不对称合成：在钙敏感受体激动剂合成中的应用。
J Org Chem. 2013 Jun 7;78(11):5314-27. doi: 10.1021/jo400371x. Epub 2013 May 13.
5
Spiroborate esters in the borane-mediated asymmetric synthesis of pyridyl and related heterocyclic alcohols.硼烷介导的吡啶基及相关杂环醇不对称合成中的螺硼酸酯
Tetrahedron Asymmetry. 2007 Nov 26;18(23):2738-2745. doi: 10.1016/j.tetasy.2007.10.044.
6
SYNTHESIS OF SPIROBORATE ESTERS FROM 1,2-AMINOALCOHOLS, ETHYLENE GLYCOL AND TRIISOPROPYL BORATE: PREPARATION OF (S)-1-(1,3,2-DIOXABOROLAN-2-YLOXY)-3-METHYL-1,1-DIPHENYLBUTAN-2-AMINE.由1,2-氨基醇、乙二醇和硼酸三异丙酯合成螺硼酸酯：(S)-1-(1,3,2-二氧杂硼戊环-2-基氧基)-3-甲基-1,1-二苯基丁烷-2-胺的制备
Organic Synth. 2010;87:26.
7
CATALYTIC ENANTIOSELECTIVE BORANE REDUCTION OF BENZYL OXIMES: PREPARATION OF (S)-1-PYRIDIN-3-YL-ETHYLAMINE BIS HYDROCHLORIDE.苄基肟的催化对映选择性硼烷还原反应：（S）-1-吡啶-3-基乙胺二盐酸盐的制备
Organic Synth. 2010 Jan 1;87:36-52.
8
A facile circular dichroism protocol for rapid determination of enantiomeric excess and concentration of chiral primary amines.一种简便的圆二色性协议，用于快速测定手性伯胺的对映体过量值和浓度。
Chemistry. 2010 Jan 4;16(1):227-32. doi: 10.1002/chem.200902650.
9
A practical and efficient route for the highly enantioselective synthesis of mexiletine analogues and novel beta-thiophenoxy and pyridyl ethers.一种实用且高效的路线，用于美西律类似物以及新型β-噻吩氧基和吡啶基醚的高对映选择性合成。
J Org Chem. 2008 Sep 5;73(17):6928-31. doi: 10.1021/jo801181d. Epub 2008 Aug 9.
10
Highly enantioselective borane reduction of heteroaryl and heterocyclic ketoxime ethers catalyzed by novel spiroborate ester derived from diphenylvalinol: application to the synthesis of nicotine analogues.由二苯基缬氨醇衍生的新型螺硼酸酯催化的杂芳基和杂环酮肟醚的高对映选择性硼烷还原反应：在尼古丁类似物合成中的应用
J Org Chem. 2008 Jun 6;73(11):4017-26. doi: 10.1021/jo800204n. Epub 2008 May 1.
聚合物负载的2-哌嗪甲醇催化硼烷对肟醚的对映选择性还原反应
J Org Chem. 2000 Sep 8;65(18):5879-81. doi: 10.1021/jo0007837.