• 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

胺类添加剂极大地扩展了亚胺不对称硅氢化反应的范围。

Amine Additives Greatly Expand the Scope of Asymmetric Hydrosilylation of Imines.

作者信息

Verdaguer Xavier, Lange Udo E W, Buchwald Stephen L

机构信息

Department of Chemistry, Massachusetts Institute of Technology, Cambridge, MA 02139 (USA), Fax: (+1) 617-253-3297.

出版信息

Angew Chem Int Ed Engl. 1998 May 4;37(8):1103-1107. doi: 10.1002/(SICI)1521-3773(19980504)37:8<1103::AID-ANIE1103>3.0.CO;2-M.

DOI:10.1002/(SICI)1521-3773(19980504)37:8<1103::AID-ANIE1103>3.0.CO;2-M
PMID:29711023
Abstract

Slow addition of a primary amine to the reaction mixture greatly increases the scope of the titanium-catalyzed asymmetric reduction of imines 1. An important added feature of this method is that chiral secondary amines 2 can be obtained in much higher optical purity (up to 99 % ee) than would be predicted from the E:Z ratios of the starting imines 1.

摘要

向反应混合物中缓慢加入伯胺可大大拓宽钛催化的亚胺1不对称还原反应的适用范围。该方法的一个重要附加特点是,与根据起始亚胺1的E:Z比例预测的结果相比,所获得的手性仲胺2的光学纯度要高得多(高达99% ee)。

相似文献

1
Amine Additives Greatly Expand the Scope of Asymmetric Hydrosilylation of Imines.胺类添加剂极大地扩展了亚胺不对称硅氢化反应的范围。
Angew Chem Int Ed Engl. 1998 May 4;37(8):1103-1107. doi: 10.1002/(SICI)1521-3773(19980504)37:8<1103::AID-ANIE1103>3.0.CO;2-M.
2
Asymmetric transfer hydrogenation of imines catalyzed by a polymer-immobilized chiral catalyst.聚合物负载手性催化剂催化的亚胺不对称转移氢化反应。
Org Biomol Chem. 2009 Jan 7;7(1):69-75. doi: 10.1039/b815407b. Epub 2008 Nov 6.
3
A method for the asymmetric hydrosilylation of N-aryl imines.
Org Lett. 2000 Mar 9;2(5):713-5. doi: 10.1021/ol005583w.
4
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.
5
Double stereodifferentiation in the catalytic asymmetric aziridination of imines prepared from α-chiral amines.手性α-胺制备的亚胺的不对称催化环氧化反应中的双重立体区分。
Chemistry. 2012 Apr 23;18(17):5302-13. doi: 10.1002/chem.201102520. Epub 2012 Mar 20.
6
Synthesis of fluorinated chiral amines using N-tert-butylsulfinyl imines.使用 N-叔丁基亚磺酰亚胺合成手性氟代胺。
Future Med Chem. 2009 Aug;1(5):875-88. doi: 10.4155/fmc.09.62.
7
An advance on exploring N-tert-butanesulfinyl imines in asymmetric synthesis of chiral amines.N-叔丁基亚磺酰亚胺在手性胺不对称合成中的研究进展。
Acc Chem Res. 2008 Jul;41(7):831-40. doi: 10.1021/ar7002623. Epub 2008 Jun 6.
8
Chiral phosphoric acid catalyzed oxidative kinetic resolution of cyclic secondary amine derivatives including tetrahydroquinolines by hydrogen transfer to imines.手性磷酸催化的环状仲胺衍生物(包括四氢喹啉)通过向亚胺转移氢进行氧化动力学拆分。
Chem Commun (Camb). 2015 Dec 4;51(93):16648-51. doi: 10.1039/c5cc06436h. Epub 2015 Oct 1.
9
Asymmetric synthesis of chiral primary amines by transfer hydrogenation of N-(tert-butanesulfinyl)ketimines.通过 N-(叔丁基亚磺酰基)亚胺的转移氢化不对称合成手性伯胺。
J Org Chem. 2010 Aug 6;75(15):5265-70. doi: 10.1021/jo101057s.
10
Asymmetric Mannich Reaction of Aryl Methyl Ketones with Cyclic Imines Benzo[e][1,2,3]oxathiazine 2,2-Dioxides Catalyzed by Cinchona Alkaloid-based Primary Amines.金鸡纳生物碱衍生的伯胺催化芳基甲基酮与环亚胺苯并[e][1,2,3]恶噻嗪2,2 -二氧化物的不对称曼尼希反应
Chem Asian J. 2016 Nov 7;11(21):3118-3125. doi: 10.1002/asia.201601149. Epub 2016 Sep 30.

引用本文的文献

1
Zirconium-Catalyzed Reductive Sulfonamidation of Amides and Its Application to Site-Selective ‑Alkylation of Pharmaceuticals.锆催化酰胺的还原磺酰胺化反应及其在药物位点选择性烷基化中的应用
ACS Catal. 2025 May 1;15(10):8150-8156. doi: 10.1021/acscatal.5c02265. eCollection 2025 May 16.
2
Enantiomerically Pure --Complexes of Transition Metals as an Effective Tool for Chirality Transfer.对映体纯——过渡金属配合物作为手性转移的有效工具
Molecules. 2025 Jun 8;30(12):2511. doi: 10.3390/molecules30122511.
3
Formal Anti-Markovnikov Addition of Water to Olefins by Titanocene-Catalyzed Epoxide Hydrosilylation: From Stoichiometric to Sustainable Catalytic Reactions.
通过二茂钛催化的环氧化合物硅氢化反应实现烯烃与水的形式反马氏加成:从化学计量反应到可持续催化反应
Glob Chall. 2023 May 2;7(7):2200240. doi: 10.1002/gch2.202200240. eCollection 2023 Jul.
4
Tackling N-Alkyl Imines with 3d Metal Catalysis: Highly Enantioselective Iron-Catalyzed Synthesis of α-Chiral Amines.用3d金属催化处理N-烷基亚胺:铁催化的α-手性胺的高对映选择性合成
Angew Chem Int Ed Engl. 2020 Sep 7;59(37):15974-15977. doi: 10.1002/anie.202006557. Epub 2020 Jun 25.
5
Early Main Group Metal Catalysts for Imine Hydrosilylation.用于亚胺硅氢化反应的早期主族金属催化剂
Chemistry. 2019 Dec 13;25(70):16141-16147. doi: 10.1002/chem.201904148. Epub 2019 Nov 18.
6
Click chemistry enables quantitative chiroptical sensing of chiral compounds in protic media and complex mixtures.点击化学能够在质子介质和复杂混合物中定量手性光学感应手性化合物。
Nat Commun. 2018 Dec 14;9(1):5323. doi: 10.1038/s41467-018-07695-9.
7
Highly diastereo- and enantioselective CuH-catalyzed synthesis of 2,3-disubstituted indolines.铜氢催化的2,3-二取代二氢吲哚的高非对映选择性和对映选择性合成。
J Am Chem Soc. 2015 Apr 15;137(14):4666-9. doi: 10.1021/jacs.5b02316. Epub 2015 Apr 6.
8
Enantioselective reduction of ketones and imines catalyzed by (CN-box)Re(V)-oxo complexes.(CN-盒)Re(V)-氧配合物催化的酮和亚胺的对映选择性还原。
Chemistry. 2010 Aug 16;16(31):9555-62. doi: 10.1002/chem.201001164.
9
Studies on the Bisoxazoline and (-)-Sparteine Mediated Enantioselective Addition of Organolithium Reagents to Imines.关于双恶唑啉和(-)-鹰爪豆碱介导的有机锂试剂对亚胺的对映选择性加成反应的研究。
Adv Synth Catal. 2008 May 5;350(7-8):1023-1045. doi: 10.1002/adsc.200800017.
10
Enantioselective hydrogenations with chiral titanocenes.使用手性二茂钛进行对映选择性氢化反应。
Molecules. 2005 Jul 14;10(6):587-619. doi: 10.3390/10060587.