用于高对映选择性[4+2]环化反应的N-杂环卡宾与手性布朗斯特酸协同催化
N-Heterocyclic Carbene and Chiral Brønsted Acid Cooperative Catalysis for a Highly Enantioselective [4+2] Annulation.
作者信息
Chen Dian-Feng, Rovis Tomislav
机构信息
Department of Chemistry, Columbia University, New York, New York 10027, United States.
出版信息
Synthesis (Stuttg). 2017 Jan;49(2):293-298. doi: 10.1055/s-0036-1588349. Epub 2016 Nov 18.
Abstract
A chiral NHC/Brønsted acid cooperative catalysis system has been developed for asymmetric annulation of functionalized benzaldehydes and activated ketones through dearomative generation of dienolate.
摘要
已开发出一种手性N - 杂环卡宾/布朗斯特酸协同催化体系，用于通过脱芳构化生成烯醇化物实现功能化苯甲醛与活性酮的不对称环化反应。
相似文献
1
N-Heterocyclic Carbene and Chiral Brønsted Acid Cooperative Catalysis for a Highly Enantioselective [4+2] Annulation.用于高对映选择性[4+2]环化反应的N-杂环卡宾与手性布朗斯特酸协同催化
Synthesis (Stuttg). 2017 Jan;49(2):293-298. doi: 10.1055/s-0036-1588349. Epub 2016 Nov 18.
2
Enantioselective Synthesis of Spirocyclohexadienones by NHC-Catalyzed Formal [3+3] Annulation Reaction of Enals.手性 N-杂环卡宾催化的烯醛的形式 [3+3] 环加成反应构建螺环环己二烯酮
Angew Chem Int Ed Engl. 2016 Jan 4;55(1):268-72. doi: 10.1002/anie.201507802. Epub 2015 Oct 21.
3
Highly Enantioselective [5 + 2] Annulations through Cooperative N-Heterocyclic Carbene (NHC) Organocatalysis and Palladium Catalysis.高对映选择性[5 + 2]环加成反应通过协同 N-杂环卡宾（NHC）有机催化和钯催化实现。
J Am Chem Soc. 2018 Mar 14;140(10):3551-3554. doi: 10.1021/jacs.8b00868. Epub 2018 Feb 28.
4
A Cooperative Ternary Catalysis System for Asymmetric Lactonizations of α-Ketoesters.用于α-酮酯不对称内酯化反应的协同三元催化体系
Adv Synth Catal. 2017 Nov 10;359(21):3713-3719. doi: 10.1002/adsc.201701015. Epub 2017 Aug 14.
5
N-Heterocyclic Carbene (NHC)-Catalyzed Transformations Involving Azolium Enolates.氮杂环卡宾（NHC）催化的涉及唑鎓烯醇盐的转化反应
Chem Rec. 2022 Aug;22(8):e202200054. doi: 10.1002/tcr.202200054. Epub 2022 May 13.
6
Cooperative catalysis of N-heterocyclic carbene and Brønsted acid for a highly enantioselective route to unprotected spiro-indoline-pyrans.氮杂环卡宾与布朗斯特酸协同催化实现无保护螺吲哚啉-吡喃的高对映选择性合成路线。
Chem Commun (Camb). 2015 May 14;51(39):8330-3. doi: 10.1039/c5cc02096d.
7
Modular Chiral -Heterocyclic Carbene Ligands for the Nickel-Catalyzed Enantioselective C-H Functionalization of Heterocycles.用于镍催化杂环对映选择性C-H官能化的模块化手性-杂环卡宾配体
Chimia (Aarau). 2020 Apr 29;74(4):278-284. doi: 10.2533/chimia.2020.278.
8
Asymmetric Redox Allylic Alkylation to Access 3,3'-Disubstituted Oxindoles Enabled by Ni/NHC Cooperative Catalysis.镍/氮杂环卡宾协同催化实现的不对称氧化还原烯丙基烷基化反应合成3,3'-二取代氧化吲哚
Angew Chem Int Ed Engl. 2022 May 23;61(22):e202201678. doi: 10.1002/anie.202201678. Epub 2022 Mar 29.
9
Enantioselective Seleno-Michael Addition Reactions Catalyzed by a Chiral Bifunctional N-Heterocyclic Carbene with Noncovalent Activation.手性双功能 N-杂环卡宾非共价活化的对映选择性硒-迈克尔加成反应。
Angew Chem Int Ed Engl. 2022 Jun 7;61(23):e202202040. doi: 10.1002/anie.202202040. Epub 2022 Apr 5.
10
Enantioselective N-heterocyclic carbene catalyzed annulation reactions with imidazolidinones.手性 N-杂环卡宾催化的与咪唑烷酮的环加成反应。
Angew Chem Int Ed Engl. 2013 Dec 16;52(51):13616-20. doi: 10.1002/anie.201307292. Epub 2013 Nov 18.
引用本文的文献
1
A (TD-)DFT study on photo-NHC catalysis: photoenolization/Diels-Alder reaction of acid fluorides catalyzed by -heterocyclic carbenes.关于光氮杂环卡宾催化的（TD-）密度泛函理论研究：由γ-杂环卡宾催化的酰氟的光烯醇化/狄尔斯-阿尔德反应
Chem Sci. 2023 Mar 15;14(15):4027-4037. doi: 10.1039/d2sc04732b. eCollection 2023 Apr 12.
2
N-Heterocyclic carbene-catalyzed enantioselective hetero-[10 + 2] annulation.氮杂环卡宾催化的对映选择性杂-[10 + 2]环化反应。
Commun Chem. 2020 Nov 27;3(1):177. doi: 10.1038/s42004-020-00425-7.
3
N-Heterocyclic carbene based catalytic platform for Hauser-Kraus annulations.用于豪泽-克劳斯环化反应的基于氮杂环卡宾的催化平台。
Chem Sci. 2020 Jun 30;11(27):7239-7243. doi: 10.1039/d0sc03116j.
4
Direct α-Acylation of Alkenes via N-Heterocyclic Carbene, Sulfinate, and Photoredox Cooperative Triple Catalysis.通过 N-杂环卡宾、亚磺酸盐和光氧化还原协同三催化实现烯烃的直接 α-酰化反应。
J Am Chem Soc. 2021 Apr 7;143(13):4903-4909. doi: 10.1021/jacs.1c01022. Epub 2021 Mar 24.
5
New Developments of the Principle of Vinylogy as Applied to π-Extended Enolate-Type Donor Systems.作为应用于π-扩展烯醇型给体体系的 vinylogy 原理的新进展。
Chem Rev. 2020 Mar 11;120(5):2448-2612. doi: 10.1021/acs.chemrev.9b00481. Epub 2020 Feb 10.
6
N-Heterocyclic Carbene Catalyzed Photoenolization/Diels-Alder Reaction of Acid Fluorides.N-杂环卡宾催化的酰氟光致烯醇化/狄尔斯-阿尔德反应
Angew Chem Int Ed Engl. 2020 Feb 17;59(8):3190-3194. doi: 10.1002/anie.201914456. Epub 2020 Jan 9.
7
Carbene-Catalyzed Enantioselective Decarboxylative Annulations to Access Dihydrobenzoxazinones and Quinolones.卡宾催化的对映选择性脱羧环化反应构建二氢苯并恶嗪酮和喹诺酮。
Angew Chem Int Ed Engl. 2019 Apr 23;58(18):5941-5945. doi: 10.1002/anie.201900600. Epub 2019 Mar 27.
8
Enantioselective -heterocyclic carbene-catalyzed nucleophilic dearomatization of alkyl pyridiniums.对映选择性 - 杂环卡宾催化的烷基吡啶鎓的亲核去芳构化反应
Chem Sci. 2017 Sep 1;8(9):6566-6569. doi: 10.1039/c7sc02648j. Epub 2017 Aug 3.
本文引用的文献
1
Annulation of o-Quinodimethanes through N-Heterocyclic Carbene Catalysis for the Synthesis of 1-Isochromanones.通过 N-杂环卡宾催化 o-醌二亚甲基的环化反应合成 1-异色满酮。
Org Lett. 2016 Sep 2;18(17):4444-7. doi: 10.1021/acs.orglett.6b02335. Epub 2016 Aug 23.
2
Insights into Stereoselective Aminomethylation Reaction of α,β-Unsaturated Aldehyde with N,O-Acetal via N-Heterocyclic Carbene and Brønsted Acid/Base Cooperative Organocatalysis.通过 N-杂环卡宾和 Brønsted 酸/碱协同有机催化对α,β-不饱和醛与 N,O-缩醛的立体选择性胺甲基化反应的深入了解。
J Org Chem. 2016 Jul 1;81(13):5370-80. doi: 10.1021/acs.joc.6b00656. Epub 2016 Jun 14.
3
Cooperative N-Heterocyclic Carbene/Palladium-Catalyzed Enantioselective Umpolung Annulations.协同 N-杂环卡宾/钯催化的对映选择性反转环加成反应。
J Am Chem Soc. 2016 Jun 29;138(25):7840-3. doi: 10.1021/jacs.6b04364. Epub 2016 Jun 15.
4
N-Heterocyclic Carbene Catalyzed Enantioselective Annulation of Benzothiazolyl Ethyl Acetates with 2-Bromoenals.N-杂环卡宾催化苯并噻唑基乙酸乙酯与2-溴烯醛的对映选择性环化反应
Synlett. 2015 Jun 11;26(11):1465-1469. doi: 10.1055/s-0034-1381004.
5
Cooperative Lewis acid/-heterocyclic carbene catalysis.协同路易斯酸/杂环卡宾催化
Chem Sci. 2012 Jan 1;3(1):53-57. doi: 10.1039/C1SC00621E.
6
Stronger Brønsted Acids: Recent Progress.更强的布朗斯特酸：近期进展
Chem Rev. 2015 Sep 9;115(17):9277-306. doi: 10.1021/acs.chemrev.5b00041. Epub 2015 Jul 16.
7
Organocatalytic Reactions Enabled by N-Heterocyclic Carbenes.氮杂环卡宾催化的有机反应
Chem Rev. 2015 Sep 9;115(17):9307-87. doi: 10.1021/acs.chemrev.5b00060. Epub 2015 May 20.
8
Enantioselective β-Protonation by a Cooperative Catalysis Strategy.通过协同催化策略实现对映选择性β-质子化
J Am Chem Soc. 2015 May 13;137(18):5891-4. doi: 10.1021/jacs.5b02887. Epub 2015 May 4.
9
Aminomethylation of enals through carbene and acid cooperative catalysis: concise access to β(2)-amino acids.亚胺通过卡宾和酸协同催化的胺甲基化反应：β(2)-氨基酸的简洁合成方法。
Angew Chem Int Ed Engl. 2015 Apr 20;54(17):5161-5. doi: 10.1002/anie.201412132. Epub 2015 Mar 3.
10
Carbon-carbon bond activation of cyclobutenones enabled by the addition of chiral organocatalyst to ketone.通过向酮中添加手性有机催化剂实现环丁烯酮的碳-碳键活化。
Nat Commun. 2015 Feb 5;6:6207. doi: 10.1038/ncomms7207.
Zotero 插件