对酮亚胺与三氯硅烷的不对称硅氢化反应的机理研究揭示了一种双重活化模型以及一种效率更高的有机催化剂。
Mechanistic investigations of the asymmetric hydrosilylation of ketimines with trichlorosilane reveals a dual activation model and an organocatalyst with enhanced efficiency.
作者信息
Li X, Reeder A T, Torri F, Adams H, Jones S
机构信息
Department of Chemistry, University of Sheffield, Dainton Building, Brook Hill, Sheffield, UK S3 7HF.
出版信息
Org Biomol Chem. 2017 Mar 15;15(11):2422-2435. doi: 10.1039/c6ob02537d.
PMID:28252158
Abstract
Structural probes used to help elucidate mechanistic information of the organocatalyzed asymmetric ketimine hydrosilylation have revealed a new catalyst with unprecedented catalytic activity, maintaining adequate performance at 0.01 mol% loading. A new 'dual activation' model has been proposed that relies on the presence of both a Lewis basic and Brønsted acidic site within the catalyst architecture.
摘要
用于帮助阐明有机催化不对称酮亚胺硅氢化反应机理信息的结构探针揭示了一种具有前所未有的催化活性的新型催化剂，在0.01 mol%负载量下仍保持足够的性能。已提出一种新的“双活化”模型，该模型依赖于催化剂结构中同时存在路易斯碱位点和布朗斯特酸位点。
相似文献
1
Mechanistic investigations of the asymmetric hydrosilylation of ketimines with trichlorosilane reveals a dual activation model and an organocatalyst with enhanced efficiency.对酮亚胺与三氯硅烷的不对称硅氢化反应的机理研究揭示了一种双重活化模型以及一种效率更高的有机催化剂。
Org Biomol Chem. 2017 Mar 15;15(11):2422-2435. doi: 10.1039/c6ob02537d.
2
The asymmetric reduction of imidazolinones with trichlorosilane.三氯硅烷对咪唑啉酮的不对称还原反应。
Chem Commun (Camb). 2017 Apr 18;53(32):4513-4516. doi: 10.1039/c7cc01561e.
3
Asymmetric reduction of ketimines with trichlorosilane employing an imidazole derived organocatalyst.使用咪唑衍生的有机催化剂通过三氯硅烷对酮亚胺进行不对称还原。
Org Biomol Chem. 2009 Jan 21;7(2):229-31. doi: 10.1039/b816051a. Epub 2008 Nov 19.
4
Role of noncovalent interactions in the enantioselective reduction of aromatic ketimines with trichlorosilane.非共价相互作用在三氯硅烷对芳香酮亚胺对映选择性还原中的作用
Org Lett. 2004 Jun 24;6(13):2253-6. doi: 10.1021/ol049213+.
5
Catalyst development for organocatalytic hydrosilylation of aromatic ketones and ketimines.用于芳烃酮和亚胺的有机催化氢化硅烷化反应的催化剂开发。
Org Biomol Chem. 2012 Jul 7;10(25):4864-77. doi: 10.1039/c2ob25472g. Epub 2012 May 17.
6
L-Valine derived chiral N-sulfinamides as effective organocatalysts for the asymmetric hydrosilylation of N-alkyl and N-aryl protected ketimines.L-缬氨酸衍生的手性N-亚磺酰胺作为N-烷基和N-芳基保护的酮亚胺不对称硅氢化反应的有效有机催化剂。
Org Biomol Chem. 2015 Jan 14;13(2):577-82. doi: 10.1039/c4ob01257g. Epub 2014 Nov 7.
7
Catalytic asymmetric mannich-type reaction of N-alkylidene-α-aminoacetonitrile with ketimines.N-亚烷基-α-氨甲基腈与亚胺的催化不对称曼尼希型反应。
Angew Chem Int Ed Engl. 2015 Apr 20;54(17):5183-6. doi: 10.1002/anie.201412377. Epub 2015 Mar 3.
8
l-Piperazine-2-carboxylic acid derived N-formamide as a highly enantioselective Lewis basic catalyst for hydrosilylation of N-aryl imines with an unprecedented substrate profile.L-哌嗪-2-羧酸衍生的N-甲酰胺作为一种对映选择性极高的路易斯碱催化剂，用于N-芳基亚胺的硅氢化反应，具有前所未有的底物范围。
Org Lett. 2006 Jul 6;8(14):3045-8. doi: 10.1021/ol060984i.
9
L-Pipecolinic acid derived Lewis base organocatalyst for asymmetric reduction of N-aryl imines by trichlorosilane: effects of the side amide group on catalytic performances.L-哌啶酸衍生的路易斯碱有机催化剂用于三氯硅烷不对称还原 N-芳基亚胺：侧酰胺基对催化性能的影响。
Org Biomol Chem. 2013 Feb 7;11(5):787-97. doi: 10.1039/c2ob26772a. Epub 2012 Dec 7.
10
Direct catalytic asymmetric addition of allyl cyanide to ketones via soft Lewis acid/hard Brønsted base/hard Lewis base catalysis.通过软路易斯酸/硬布朗斯特碱/硬路易斯碱催化，实现了酮的直接催化不对称烯丙基氰化加成反应。
J Am Chem Soc. 2010 Apr 21;132(15):5522-31. doi: 10.1021/ja101687p.
引用本文的文献
1
Rational Design of Simple Organocatalysts for the HSiCl Enantioselective Reduction of (E)--(1-Phenylethylidene)aniline.简单有机催化剂的合理设计用于 HSiCl 对（E）-（1-苯亚乙基）苯胺的对映选择性还原。
Molecules. 2021 Nov 18;26(22):6963. doi: 10.3390/molecules26226963.
Zotero 插件