具有穹顶双菲咯啉镁磷酸盐盐的催化不对称氮杂-Darzens 反应。
Catalytic asymmetric aza-Darzens reaction with a vaulted biphenanthrol magnesium phosphate salt.
机构信息
Department of Chemistry, University of South Florida, 4202 East Fowler Avenue CHE205A, Tampa, Florida 33620, United States.
出版信息
Org Lett. 2011 May 6;13(9):2188-91. doi: 10.1021/ol200407r. Epub 2011 Apr 5.
Abstract
Conditions for a catalytic asymmetric aza-Darzens aziridine synthesis mediated by a vaulted biphenanthrol (VAPOL) magnesium phosphate salt is described. Using simple substrates, this methodology explores the scope and reactivity of a new magnesium catalyst for an aziridination reaction capable of building chirality and complexity simultaneously.
摘要
描述了由穹顶联苯酚（VAPOL）镁磷酸盐盐介导的催化不对称氮杂-Darzens 氮丙啶合成的条件。使用简单的底物，该方法探讨了一种新的镁催化剂在能够同时构建手性和复杂性的氮丙啶反应中的范围和反应性。
相似文献
1
Catalytic asymmetric aza-Darzens reaction with a vaulted biphenanthrol magnesium phosphate salt.具有穹顶双菲咯啉镁磷酸盐盐的催化不对称氮杂-Darzens 反应。
Org Lett. 2011 May 6;13(9):2188-91. doi: 10.1021/ol200407r. Epub 2011 Apr 5.
2
Catalytic asymmetric aziridination with borate catalysts derived from VANOL and VAPOL ligands: scope and mechanistic studies.基于VANOL和VAPOL配体的硼酸盐催化剂催化的不对称氮杂环丙烷化反应：范围及机理研究
Chemistry. 2008;14(12):3785-803. doi: 10.1002/chem.200701558.
3
Direct access to N-H-aziridines from asymmetric catalytic aziridination with borate catalysts derived from vaulted binaphthol and vaulted biphenanthrol ligands.通过使用源自拱形联萘酚和拱形联菲罗啉配体的硼酸盐催化剂进行不对称催化氮杂环丙烷化反应直接制备N - H - 氮杂环丙烷。
J Am Chem Soc. 2007 Jun 6;129(22):7185-94. doi: 10.1021/ja069371r. Epub 2007 May 12.
4
An asymmetric Diels-Alder reaction catalyzed by chiral phosphate magnesium complexes: highly enantioselective synthesis of chiral spirooxindoles.手性磷酸镁配合物催化的不对称 Diels-Alder 反应：手性螺环氧化吲哚的高对映选择性合成。
Angew Chem Int Ed Engl. 2013 Apr 22;52(17):4628-32. doi: 10.1002/anie.201209295. Epub 2013 Mar 20.
5
Efficient Access to Chiral Trisubstituted Aziridines via Catalytic Enantioselective Aza-Darzens Reactions.通过催化对映选择性氮杂-Darzens 反应高效获得手性三取代氮丙啶。
Angew Chem Int Ed Engl. 2017 Feb 20;56(9):2440-2444. doi: 10.1002/anie.201607845. Epub 2017 Jan 23.
6
A Nanovessel-Catalyzed Three-Component Aza-Darzens Reaction.纳米载体催化的三组分氮杂-Darzens 反应。
J Am Chem Soc. 2020 Jan 15;142(2):733-737. doi: 10.1021/jacs.9b13177. Epub 2020 Jan 7.
7
Diastereoselective Synthesis of α-Quaternary Aziridine-2-carboxylates via Aza-Corey-Chaykovsky Aziridination of N-tert-Butanesulfinyl Ketimino Esters.通过 N-叔丁基亚磺酰基酮亚胺酯的氮杂-Corey-Chaykovsky 氮丙啶化反应，对映选择性合成α-季碳氮丙啶-2-羧酸酯。
Org Lett. 2015 Nov 20;17(22):5614-7. doi: 10.1021/acs.orglett.5b02838. Epub 2015 Nov 11.
8
The asymmetric aza-Claisen rearrangement: development of widely applicable pentaphenylferrocenyl palladacycle catalysts.不对称氮杂克莱森重排：广泛适用的五苯基二茂铁基钯环催化剂的开发
Chemistry. 2009 Sep 7;15(35):8722-41. doi: 10.1002/chem.200900712.
9
BOROX catalysis: self-assembled amino-BOROX and imino-BOROX chiral Brønsted acids in a five component catalyst assembly/catalytic asymmetric aziridination.硼氧烷催化：自组装的氨基酸硼氧烷和亚氨基硼氧烷手性 Brønsted 酸在五组分催化剂组装/催化不对称氮丙啶化中的应用。
J Org Chem. 2012 Sep 21;77(18):7932-44. doi: 10.1021/jo301064u. Epub 2012 Sep 4.
10
New sugar-derived bifunctional chiral ureas as highly effective organocatalysts in asymmetric aza-Henry reaction.新型糖基衍生双功能手性脲作为不对称氮杂-Henry反应中的高效有机催化剂
Carbohydr Res. 2015 Mar 2;404:83-6. doi: 10.1016/j.carres.2014.11.019. Epub 2014 Dec 31.
引用本文的文献
1
Recent Developments in Catalytic Asymmetric Aziridination.催化不对称氮杂环丙烷化反应的最新进展
Top Curr Chem (Cham). 2025 Sep 10;383(4):40. doi: 10.1007/s41061-025-00519-7.
2
Highly Efficient Darzens Reactions Mediated by Phosphazene Bases under Mild Conditions.磷杂环戊二烯基碱介导下温和条件下的高立体选择性达参反应。
ChemistryOpen. 2022 Oct;11(10):e202200179. doi: 10.1002/open.202200179.
3
3-Arylaziridine-2-carboxylic Acid Derivatives and (3-Arylaziridin-2-yl)ketones: The Aziridination Approaches.3-芳基氮丙啶-2-羧酸衍生物和(3-芳基氮丙啶-2-基)酮：氮丙啶化方法。
Int J Mol Sci. 2021 Sep 13;22(18):9861. doi: 10.3390/ijms22189861.
4
Direct asymmetric N-propargylation of indoles and carbazoles catalyzed by lithium SPINOL phosphate.手性磷酸锂催化吲哚和咔唑的不对称 N-丙炔基化反应。
Nat Commun. 2020 Jan 13;11(1):226. doi: 10.1038/s41467-019-13886-9.
5
The Effect of Nano-Particles and Water Glass on the Water Stability of Magnesium Phosphate Cement Based Mortar.纳米颗粒和水玻璃对磷酸镁水泥基砂浆水稳定性的影响
Materials (Basel). 2019 Nov 14;12(22):3755. doi: 10.3390/ma12223755.
6
Efficient Access to Chiral Trisubstituted Aziridines via Catalytic Enantioselective Aza-Darzens Reactions.通过催化对映选择性氮杂-Darzens 反应高效获得手性三取代氮丙啶。
Angew Chem Int Ed Engl. 2017 Feb 20;56(9):2440-2444. doi: 10.1002/anie.201607845. Epub 2017 Jan 23.
7
Lithium BINOL phosphate catalyzed desymmetrization of meso-epoxides with aromatic thiols.手性联二萘酚磷酸锂催化的芳香硫醇对消旋环氧的不对称开环反应。
Org Lett. 2014 Nov 7;16(21):5548-51. doi: 10.1021/ol502527q. Epub 2014 Oct 15.
8
Catalytic asymmetric α-Iminol rearrangement: new chiral platforms.催化不对称α-亚胺醇重排：新型手性平台
J Am Chem Soc. 2014 Oct 8;136(40):13971-4. doi: 10.1021/ja5065685. Epub 2014 Sep 23.
9
Asymmetric one-pot synthesis of 1,3-oxazolidines and 1,3-oxazinanes via hemiaminal intermediates.通过半胺中间体实现1,3-恶唑烷和1,3-恶嗪烷的不对称一锅法合成。
Org Lett. 2014 Aug 15;16(16):4098-101. doi: 10.1021/ol501789c. Epub 2014 Jul 30.
10
Vaulted biaryls in catalysis: A structure-activity relationship guided tour of the immanent domain of the VANOL ligand.催化中的拱形联芳烃：范诺配体内在领域的结构-活性关系考察。
Chemistry. 2013 Nov 11;19(46):15565-71. doi: 10.1002/chem.201302451. Epub 2013 Oct 2.
本文引用的文献
1
Highly enantioselective catalytic benzoyloxylation of 3-aryloxindoles using chiral VAPOL calcium phosphate.使用手性VAPOL磷酸钙对3-芳基氧化吲哚进行高度对映选择性催化苯甲酰氧基化反应。
Angew Chem Int Ed Engl. 2011 Feb 1;50(5):1135-8. doi: 10.1002/anie.201006595. Epub 2010 Dec 22.
2
Chiral calcium organophosphate-catalyzed enantioselective electrophilic amination of enamides.手性钙有机膦催化的烯酰胺对映选择性亲电胺化反应。
Org Lett. 2011 Jan 7;13(1):94-7. doi: 10.1021/ol102625s. Epub 2010 Dec 1.
3
Synthesis and structural aspects of N-triflylphosphoramides and their calcium salts--highly acidic and effective Brønsted acids.N-三氟甲磺酸磷酰胺及其钙盐的合成与结构研究--高酸性和有效的布朗斯台德酸。
Chemistry. 2010 Nov 22;16(44):13116-26. doi: 10.1002/chem.201001438.
4
How the binding of substrates to a chiral polyborate counterion governs diastereoselection in an aziridination reaction: H-bonds in equipoise.手性聚硼酸盐抗衡离子与底物的结合如何控制氮丙啶反应中的非对映选择性：平衡中的氢键。
J Am Chem Soc. 2010 Sep 29;132(38):13104-7. doi: 10.1021/ja103863j.
5
Unifying metal and Brønsted acid catalysis--concepts, mechanisms, and classifications.统一金属和布朗斯特酸催化——概念、机制和分类。
Chemistry. 2010 Aug 16;16(31):9350-65. doi: 10.1002/chem.201001140.
6
Which is the actual catalyst: chiral phosphoric Acid or chiral calcium phosphate?
Angew Chem Int Ed Engl. 2010 May 17;49(22):3823-6. doi: 10.1002/anie.201000824.
7
Stereoselective synthesis of trisubstituted aziridines with N-alpha-diazoacyl camphorsultam.用 N-α-重氮酰基樟脑磺酰胺立体选择性合成三取代氮丙啶。
Org Lett. 2010 Apr 16;12(8):1668-71. doi: 10.1021/ol100104v.
8
To protonate or alkylate? Stereoselective Brønsted acid catalysis of C-C bond formation using diazoalkanes.质子化还是烷基化？使用重氮烷烃进行 C-C 键形成的立体选择性布朗斯特酸催化。
Angew Chem Int Ed Engl. 2010 Mar 22;49(13):2290-8. doi: 10.1002/anie.200904828.
9
Asymmetric binary-acid catalysis with chiral phosphoric acid and MgF(2): catalytic enantioselective Friedel-Crafts reactions of beta,gamma-unsaturated alpha-ketoesters.手性磷酸和氟化镁的不对称双酸催化：β,γ-不饱和α-酮酯的催化对映选择性傅克反应。
Org Lett. 2010 Mar 5;12(5):1096-9. doi: 10.1021/ol1000928.
10
Chiral lithium(I) binaphtholate salts for the enantioselective direct Mannich-type reaction with a change of syn/anti and absolute stereochemistry.手性锂（I）联萘酚盐用于对映选择性直接曼尼希型反应，其中顺/反和绝对立体化学发生变化。
J Am Chem Soc. 2010 Jan 13;132(1):56-7. doi: 10.1021/ja909874b.
Zotero 插件