• 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

首例高度对映选择性均相催化不对称还原胺化反应:α-N-苄基氨基酸的合成

The first highly enantioselective homogeneously catalyzed asymmetric reductive amination: synthesis of alpha-N-benzylamino acids.

作者信息

Kadyrov Renat, Riermeier Thomas H, Dingerdissen Uwe, Tararov Vitali, Börner Armin

机构信息

Degussa AG, Project House Catalysis, Industriepark Höchst, G 830, D-65926 Frankfurt/Main, Germany.

出版信息

J Org Chem. 2003 May 16;68(10):4067-70. doi: 10.1021/jo020690k.

DOI:10.1021/jo020690k
PMID:12737592
Abstract

High-throughput screening considering a library of 96 chiral P-ligands involved in two types of Rh(I) complexes was used for the identification of homogeneous catalysts for the highly enantioselective reductive amination of alpha-keto acids with benzylamine. After optimization of the reaction conditions and scale-up with a cationic Rh-Deguphos catalyst, a range of chiral alpha-amino acids could be produced by this new reaction in good yield and by up to 98% ee.

摘要

通过高通量筛选,研究了96种参与两种铑(I)配合物的手性磷配体库,用于鉴定α-酮酸与苄胺的高对映选择性还原胺化反应的均相催化剂。在用阳离子铑-德古磷催化剂优化反应条件并放大规模后,通过这种新反应可以以良好的产率和高达98%的对映体过量(ee)制备一系列手性α-氨基酸。

相似文献

1
The first highly enantioselective homogeneously catalyzed asymmetric reductive amination: synthesis of alpha-N-benzylamino acids.首例高度对映选择性均相催化不对称还原胺化反应:α-N-苄基氨基酸的合成
J Org Chem. 2003 May 16;68(10):4067-70. doi: 10.1021/jo020690k.
2
Combinatorial design of simplified high-performance chiral phase-transfer catalysts for practical asymmetric synthesis of alpha-alkyl- and alpha,alpha-dialkyl-alpha-amino acids.用于α-烷基和α,α-二烷基-α-氨基酸实际不对称合成的简化高性能手性相转移催化剂的组合设计
Chem Asian J. 2008 Sep 1;3(8-9):1702-14. doi: 10.1002/asia.200800107.
3
Asymmetric α-amination of 4-substituted pyrazolones catalyzed by a chiral Gd(OTf)3/N,N'-dioxide complex: highly enantioselective synthesis of 4-amino-5-pyrazolone derivatives.手性 Gd(OTf)3/N,N'-二氧杂环戊烷配合物催化 4-取代吡唑酮的不对称 α-胺化反应:4-氨基-5-吡唑酮衍生物的高对映选择性合成。
Org Lett. 2011 Feb 18;13(4):596-9. doi: 10.1021/ol102804p. Epub 2011 Jan 7.
4
Highly enantioselective reductive amination of simple aryl ketones catalyzed by Ir-f-Binaphane in the presence of titanium(IV) isopropoxide and iodine.在异丙醇钛(IV)和碘存在下,Ir-f-联萘催化简单芳基酮的高对映选择性还原胺化反应。
J Org Chem. 2003 May 16;68(10):4120-2. doi: 10.1021/jo026856z.
5
An easy approach to optically active alpha-amino phosphonic acid derivatives by chiral Zn(II)-catalyzed enantioselective amination of phosphonates.通过手性锌(II)催化的膦酸酯对映选择性胺化反应制备光学活性α-氨基膦酸衍生物的简便方法。
J Am Chem Soc. 2005 Apr 27;127(16):5772-3. doi: 10.1021/ja050989v.
6
Mimicking enzymatic transaminations: attempts to understand and develop a catalytic asymmetric approach to chiral alpha-amino acids.模拟酶促转氨作用:理解和开发手性α-氨基酸催化不对称合成方法的尝试。
Org Biomol Chem. 2004 Jul 21;2(14):2044-9. doi: 10.1039/b404381b. Epub 2004 Jun 21.
7
Direct asymmetric reductive amination.直接不对称还原胺化反应。
J Am Chem Soc. 2009 Aug 19;131(32):11316-7. doi: 10.1021/ja905143m.
8
Highly regioselective, catalytic asymmetric reductive coupling of 1,3-enynes and ketones.1,3-烯炔与酮的高度区域选择性催化不对称还原偶联反应。
Org Lett. 2005 Jul 7;7(14):3077-80. doi: 10.1021/ol051075g.
9
Rh-catalyzed asymmetric hydrogenation of gamma-phthalimido-substituted alpha,beta-unsaturated carboxylic acid esters: an efficient enantioselective synthesis of beta-aryl-gamma-amino acids.铑催化的γ-邻苯二甲酰亚胺取代的α,β-不饱和羧酸酯的不对称氢化反应:β-芳基-γ-氨基酸的高效对映选择性合成
Org Lett. 2007 Nov 8;9(23):4825-8. doi: 10.1021/ol702193v. Epub 2007 Oct 12.
10
Rh-catalyzed enantioselective conjugate addition of arylboronic acids with a dynamic library of chiral tropos phosphorus ligands.铑催化芳基硼酸与手性对流磷配体动态库的对映选择性共轭加成反应。
Chemistry. 2007;13(5):1547-58. doi: 10.1002/chem.200600960.

引用本文的文献

1
Engineered C-N Lyases for Stereoselective Synthesis of Tertiary Amines.用于立体选择性合成叔胺的工程化C-N裂解酶
Angew Chem Int Ed Engl. 2025 Aug 18;64(34):e202507311. doi: 10.1002/anie.202507311. Epub 2025 Jul 4.
2
Molybdenum-Catalyzed Asymmetric Amination of α-Hydroxy Esters: Synthesis of α-Amino Acids.钼催化α-羟基酯的不对称胺化反应:α-氨基酸的合成
Adv Sci (Weinh). 2025 May;12(18):e2403437. doi: 10.1002/advs.202403437. Epub 2025 Mar 10.
3
Iridium-catalyzed direct asymmetric reductive amination utilizing primary alkyl amines as the N-sources.
铱催化的利用伯烷基胺作为氮源的直接不对称还原胺化反应。
Nat Commun. 2022 Jun 10;13(1):3344. doi: 10.1038/s41467-022-31045-5.
4
Intramolecular asymmetric reductive amination: synthesis of enantioenriched dibenz[,]azepines.分子内不对称还原胺化反应:对映体富集的二苯并[,]氮杂卓的合成
Chem Sci. 2018 Dec 27;10(8):2473-2477. doi: 10.1039/c8sc04482a. eCollection 2019 Feb 28.
5
Bifunctional catalysis: direct reductive amination of aliphatic ketones with an iridium-phosphate catalyst.双功能催化:使用铱-磷酸盐催化剂直接还原胺化脂肪酮。
Molecules. 2010 Apr 8;15(4):2453-72. doi: 10.3390/molecules15042453.