用于烯醇酸酯环化反应的协同N-杂环卡宾/手性磷酸催化体系。
A cooperative N-heterocyclic carbene/chiral phosphate catalysis system for allenolate annulations.
作者信息
Lee Anna, Scheidt Karl A
机构信息
Department of Chemistry Center for Molecular Innovation and Drug Discovery, Northwestern University, 2145 Sheridan Road, Evanston, IL 60208 (USA).
出版信息
Angew Chem Int Ed Engl. 2014 Jul 14;53(29):7594-8. doi: 10.1002/anie.201403446. Epub 2014 Jun 4.
Abstract
The highly enantioselective NHC-catalyzed [3+2] annulation reaction with α,β-alkynals and α-ketoesters has been developed. A new mode of cooperative catalysis involving the combination of a chiral Brønsted acid and a C1-symmetric biaryl saturated-imidazolium precatalyst was required to generate the desired γ-crotonolactones in high yields and levels of enantioselectivity.
摘要
已开发出高度对映选择性的氮杂环卡宾（NHC）催化的与α,β-炔醛和α-酮酯的[3+2]环化反应。需要一种涉及手性布朗斯特酸和C1对称联芳基饱和咪唑鎓预催化剂组合的协同催化新模式，以高产率和对映选择性水平生成所需的γ-巴豆内酯。
相似文献
1
A cooperative N-heterocyclic carbene/chiral phosphate catalysis system for allenolate annulations.用于烯醇酸酯环化反应的协同N-杂环卡宾/手性磷酸催化体系。
Angew Chem Int Ed Engl. 2014 Jul 14;53(29):7594-8. doi: 10.1002/anie.201403446. Epub 2014 Jun 4.
2
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.
3
N-Heterocyclic carbene-catalyzed enantioselective annulations: a dual activation strategy for a formal [4+2] addition for dihydrocoumarins.N-杂环卡宾催化的对映选择性环化反应：一种用于二氢香豆素形式[4+2]加成的双重活化策略。
Chem Commun (Camb). 2015 Feb 25;51(16):3407-10. doi: 10.1039/c4cc09590a.
4
Asymmetric homoenolate additions to acyl phosphonates through rational design of a tailored N-heterocyclic carbene catalyst.通过对定制 N-杂环卡宾催化剂的合理设计，实现了不对称偕同羟醛加成到酰基膦酸酯。
J Am Chem Soc. 2014 Jan 8;136(1):76-9. doi: 10.1021/ja410932t. Epub 2013 Dec 17.
5
Kinetic resolution of 1,1'-biaryl-2,2'-diols and amino alcohols through NHC-catalyzed atroposelective acylation.通过 NHC 催化的手性选择性酰化反应拆分 1,1'-联苯-2,2'-二醇和氨基醇。
Angew Chem Int Ed Engl. 2014 Oct 6;53(41):11041-5. doi: 10.1002/anie.201406192. Epub 2014 Aug 21.
6
N-heterocyclic carbene catalyzed [4+3] annulation of enals and o-quinone methides: highly enantioselective synthesis of benzo-ε-lactones.N-杂环卡宾催化烯醛与邻醌甲基化物的[4+3]环化反应：苯并-ε-内酯的高对映选择性合成
Angew Chem Int Ed Engl. 2013 Aug 12;52(33):8607-10. doi: 10.1002/anie.201303903. Epub 2013 Jul 1.
7
N-Heterocyclic Carbene (NHC)/Metal Cooperative Catalysis.N-杂环卡宾（NHC）/金属协同催化。
Top Curr Chem (Cham). 2019 Nov 13;377(6):35. doi: 10.1007/s41061-019-0266-z.
8
Stereospecific asymmetric N-heterocyclic carbene (NHC)-catalyzed redox synthesis of trifluoromethyl dihydropyranones and mechanistic insights.立体选择性不对称 N-杂环卡宾 (NHC)-催化的三氟甲基二氢吡喃酮的氧化还原合成及机理研究。
J Org Chem. 2013 Sep 20;78(18):9243-57. doi: 10.1021/jo401433q. Epub 2013 Sep 3.
9
N-Heterocyclic carbene-catalyzed [3 + 2] annulation of bromoenals with 3-aminooxindoles: highly enantioselective synthesis of spirocyclic oxindolo-γ-lactams.N-杂环卡宾催化溴代烯醛与3-氨基氧化吲哚的[3+2]环化反应：螺环氧化吲哚-γ-内酰胺的高对映选择性合成
Org Biomol Chem. 2016 Feb 14;14(6):2007-14. doi: 10.1039/c5ob02466h.
10
Bifunctional N-Heterocyclic Carbenes Derived from l-Pyroglutamic Acid and Their Applications in Enantioselective Organocatalysis.源自L-焦谷氨酸的双功能N-杂环卡宾及其在对映选择性有机催化中的应用
Acc Chem Res. 2020 Mar 17;53(3):690-702. doi: 10.1021/acs.accounts.9b00635. Epub 2020 Mar 6.
引用本文的文献
1
A C-symmetric -heterocyclic carbene catalysed oxidative spiroannulation of isatin-derived enals: highly enantioselective synthesis of spirooxindole δ-lactones.一种C-对称-杂环卡宾催化的异吲哚酮衍生烯醛的氧化螺环化反应：螺环氧化吲哚δ-内酯的高对映选择性合成。
RSC Adv. 2018 Apr 24;8(28):15444-15447. doi: 10.1039/c8ra02009d. eCollection 2018 Apr 23.
2
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.
3
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.
4
Calcium(ii)-catalyzed enantioselective conjugate additions of amines.钙（II）催化的胺的对映选择性共轭加成反应。
Chem Sci. 2018 Jan 10;9(6):1634-1639. doi: 10.1039/c7sc05205g. eCollection 2018 Feb 14.
5
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.
6
N-Heterocyclic carbene-catalyzed enantioselective annulations: a dual activation strategy for a formal [4+2] addition for dihydrocoumarins.N-杂环卡宾催化的对映选择性环化反应：一种用于二氢香豆素形式[4+2]加成的双重活化策略。
Chem Commun (Camb). 2015 Feb 25;51(16):3407-10. doi: 10.1039/c4cc09590a.
7
Enantioconvergent synthesis of functionalized γ-butyrolactones via (3 + 2)-annulation.通过(3 + 2)环化反应对官能化γ-丁内酯进行对映汇聚式合成。
J Am Chem Soc. 2015 Jan 14;137(1):122-5. doi: 10.1021/ja511701j. Epub 2014 Dec 23.
本文引用的文献
1
Asymmetric homoenolate additions to acyl phosphonates through rational design of a tailored N-heterocyclic carbene catalyst.通过对定制 N-杂环卡宾催化剂的合理设计，实现了不对称偕同羟醛加成到酰基膦酸酯。
J Am Chem Soc. 2014 Jan 8;136(1):76-9. doi: 10.1021/ja410932t. Epub 2013 Dec 17.
2
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.
3
Theoretical study on the acidities of chiral phosphoric acids in dimethyl sulfoxide: hints for organocatalysis.手性磷酸在二甲亚砜中的酸性的理论研究：对有机催化的启示。
J Org Chem. 2013 Jul 19;78(14):7076-85. doi: 10.1021/jo400915f. Epub 2013 Jul 1.
4
An efficient approach to the securinega alkaloids empowered by cooperative N-heterocyclic carbene/Lewis acid catalysis.一种由协同的氮杂环卡宾/路易斯酸催化实现的喜树碱类生物碱的高效合成方法。
Angew Chem Int Ed Engl. 2013 May 27;52(22):5789-94. doi: 10.1002/anie.201301849. Epub 2013 Apr 22.
5
Exploiting Acyl and Enol Azolium Intermediates via NHeterocyclic Carbene Catalyzed Reactions of Alpha-Reducible Aldehydes.通过氮杂环卡宾催化的α-可还原醛反应利用酰基和烯醇氮鎓中间体
Adv Synth Catal. 2012 Jun 18;354(9):1617-1639. doi: 10.1002/adsc.201200031. Epub 2012 Apr 19.
6
N-heterocyclic carbene (NHC)-catalyzed/Lewis acid mediated conjugate umpolung of alkynyl aldehydes for the synthesis of butenolides: a formal [3+2] annulation.N-杂环卡宾（NHC）催化/Lewis 酸介导的炔基醛的共轭反转合成丁烯内酯：一种形式的[3+2]环加成。
Chemistry. 2013 Mar 25;19(13):4146-50. doi: 10.1002/chem.201204386. Epub 2013 Feb 27.
7
Asymmetric counteranion-directed catalysis: concept, definition, and applications.不对称抗衡阴离子导向催化：概念、定义和应用。
Angew Chem Int Ed Engl. 2013 Jan 7;52(2):518-33. doi: 10.1002/anie.201205343. Epub 2012 Nov 28.
8
Asymmetric ion-pairing catalysis.不对称离子对催化。
Angew Chem Int Ed Engl. 2013 Jan 7;52(2):534-61. doi: 10.1002/anie.201205449. Epub 2012 Nov 28.
9
Controlled β-protonation and [4+2] cycloaddition of enals and chalcones via N-heterocyclic carbene/acid catalysis: toward substrate independent reaction control.通过 N-杂环卡宾/酸催化控制β-质子化和烯醛与查尔酮的[4+2]环加成反应：实现底物无关的反应控制。
Chem Commun (Camb). 2013 Jan 11;49(3):261-3. doi: 10.1039/c2cc36564b. Epub 2012 Nov 22.
10
Asymmetric binary acid catalysis: chiral phosphoric acid as dual ligand and acid.不对称双酸催化：手性磷酸作为双配体和酸。
Chem Commun (Camb). 2013 Jan 30;49(9):847-58. doi: 10.1039/c2cc34288j.
Zotero 插件