Lewis Acid-Catalyzed Reductive Amination of Aldehydes and Ketones with N ,N -Dimethylformamide as Dimethylamino Source, Reductant and Solvent

2018 ◽  
Vol 360 (3) ◽  
pp. 485-490 ◽  
Author(s):  
Luo Yang ◽  
Jie Lin ◽  
Lei Kang ◽  
Wang Zhou ◽  
Da-You Ma
Keyword(s):  
Lewis Acid ◽  
Reductive Amination ◽  
Aldehydes And Ketones ◽  
Acid Catalyzed

scholarly journals Lewis Acid-Catalyzed Intermolecular [4 + 2] Cycloaddition of 3-Alkoxycyclobutanones to Aldehydes and Ketones

2008 ◽  
Vol 130 (41) ◽  
pp. 13810-13810
Author(s):  
Jun-ichi Matsuo ◽  
Shun Sasaki ◽  
Hiroyuki Tanaka ◽  
Hiroyuki Ishibashi
Keyword(s):  
Lewis Acid ◽  
Aldehydes And Ketones ◽  
Acid Catalyzed

Lewis acid-catalyzed Meyer–Schuster reactions: methodology for the olefination of aldehydes and ketones

Tetrahedron ◽  
2008 ◽  
Vol 64 (29) ◽  
pp. 6988-6996 ◽  
Author(s):  
Douglas A. Engel ◽  
Susana S. Lopez ◽  
Gregory B. Dudley
Keyword(s):  
Lewis Acid ◽  
Aldehydes And Ketones ◽  
Acid Catalyzed

Lewis Acid-Catalyzed Intermolecular [4 + 2] Cycloaddition of 3-Alkoxycyclobutanones to Aldehydes and Ketones

2008 ◽  
Vol 130 (35) ◽  
pp. 11600-11601 ◽  
Author(s):  
Jun-ichi Matsuo ◽  
Shun Sasaki ◽  
Hiroyuki Tanaka ◽  
Hiroyuki Ishibashi
Keyword(s):  
Lewis Acid ◽  
Aldehydes And Ketones ◽  
Acid Catalyzed

Lewis Acid-Catalyzed Reductive Amination of Carbonyl Compounds with Aminohydrosilanes

Synlett ◽  
2001 ◽  
Vol 2001 (10) ◽  
pp. 1617-1619 ◽  
Author(s):  
Katsukiyo Miura ◽  
Kazunori Ootsuka ◽  
Shuntaro Suda ◽  
Hisashi Nishikori ◽  
Akira Hosomi
Keyword(s):  
Lewis Acid ◽  
Carbonyl Compounds ◽  
Reductive Amination ◽  
Acid Catalyzed

ChemInform Abstract: Lewis Acid-Catalyzed Intermolecular [4 + 2] Cycloaddition of 3-Alkoxycyclobutanones to Aldehydes and Ketones.

ChemInform ◽  
2009 ◽  
Vol 40 (2) ◽  
Author(s):  
Jun-ichi Matsuo ◽  
Shun Sasaki ◽  
Hiroyuki Tanaka ◽  
Hiroyuki Ishibashi
Keyword(s):  
Lewis Acid ◽  
Aldehydes And Ketones ◽  
Acid Catalyzed

ChemInform Abstract: Studies on Organosilicon Chemistry. Part 155. Lewis Acid Catalyzed Reductive Amination of Carbonyl Compounds with Aminohydrosilanes.

ChemInform ◽  
2010 ◽  
Vol 33 (7) ◽  
pp. no-no
Author(s):  
Katsukiyo Miura ◽  
Kazunori Ootsuka ◽  
Shuntaro Suda ◽  
Hisashi Nishikori ◽  
Akira Hosomi
Keyword(s):  
Lewis Acid ◽  
Carbonyl Compounds ◽  
Reductive Amination ◽  
Acid Catalyzed ◽  
Organosilicon Chemistry

scholarly journals Asymmetric Lewis acid-catalyzed 1,3-dipolar cycloadditions

2008 ◽  
Vol 80 (5) ◽  
pp. 1013-1018 ◽  
Author(s):  
Andrei Bădoiu ◽  
Yasmin Brinkmann ◽  
Florian Viton ◽  
E. Peter Kündig
Keyword(s):  
Transition Metal ◽  
Lewis Acid ◽  
Lewis Acids ◽  
Cycloaddition Reaction ◽  
Diels Alder ◽  
Dipolar Cycloaddition ◽  
Dipolar Cycloadditions ◽  
Asymmetric Catalytic ◽  
Aldehydes And Ketones ◽  
Acid Catalyzed

Highly tuned, one-point binding chiral iron and ruthenium complexes selectively coordinate and activate α,β-unsaturated aldehydes and ketones toward asymmetric catalytic Diels-Alder cycloaddition reactions. Here we focus on the application of these transition-metal Lewis acids to asymmetric catalytic 1,3-dipolar cycloaddition reaction between enals and cyclic and acyclic nitrones as well as aryl nitrile oxides to give isoxazolidines and isoxazolines, respectively.

Catalytic Carbonyl-Olefin Metathesis of Aliphatic Ketones: Iron(III) HomoDimers as Lewis Acidic Superelectrophiles

2018 ◽  
Author(s):  
Haley Albright ◽  
Paul S. Riehl ◽  
Christopher C. McAtee ◽  
Jolene P. Reid ◽  
Jacob R. Ludwig ◽  
...  
Keyword(s):  
Lewis Acid ◽  
Olefin Metathesis ◽  
Acid Activation ◽  
Lewis Acid Catalysts ◽  
Distinct Mode ◽  
Aliphatic Ketones ◽  
Carbon Carbon Bond ◽  
Metathesis Reactions ◽  
Acid Catalyzed

<div>Catalytic carbonyl-olefin metathesis reactions have recently been developed as a powerful tool for carbon-carbon bond</div><div>formation. However, currently available synthetic protocols rely exclusively on aryl ketone substrates while the corresponding aliphatic analogs remain elusive. We herein report the development of Lewis acid-catalyzed carbonyl-olefin ring-closing metathesis reactions for aliphatic ketones. Mechanistic investigations are consistent with a distinct mode of activation relying on the in situ formation of a homobimetallic singly-bridged iron(III)-dimer as the active catalytic species. These “superelectrophiles” function as more powerful Lewis acid catalysts that form upon association of individual iron(III)-monomers. While this mode of Lewis acid activation has previously been postulated to exist, it has not yet been applied in a catalytic setting. The insights presented are expected to enable further advancement in Lewis acid catalysis by building upon the activation principle of “superelectrophiles” and broaden the current scope of catalytic carbonyl-olefin metathesis reactions.</div>

Computationally-Guided Investigation of Dual Amine/pi Lewis Acid Catalysts for Direct Additions of Aldehydes and Ketones to Unactivated Alkenes and Alkynes

2020 ◽  
Author(s):  
Eric Greve ◽  
Jacob D. Porter ◽  
Chris Dockendorff
Keyword(s):  
Lewis Acid ◽  
Density Functional ◽  
Acid Catalyst ◽  
Metal Catalyst ◽  
Catalyst Poisoning ◽  
Lewis Acid Catalysts ◽  
Metal Ligands ◽  
Aldehydes And Ketones ◽  
Lewis Acid Catalyst ◽  
Catalyst Systems

Dual amine/pi Lewis acid catalyst systems have been reported for intramolecular direct additions of aldehydes/ketones to unactivated alkynes and occasionally alkenes, but related intermolecular reactions are rare and not presently of significant synthetic utility, likely due to undesired coordination of enamine intermediates to the metal catalyst. We reasoned that bulky metal ligands and bulky amine catalysts could minimize catalyst poisoning and could facilitate certain examples of direct intermolecular additions of aldehyde/ketones to alkenes/alkynes. Density Functional Theory (DFT) calculations were performed that suggested that PyBOX-Pt(II) catalysts for alkene/alkyne activation could be combined with MacMillan’s imidazolidinone organocatalyst for aldehyde/ketone activation to facilitate desirable C-C bond formations, and certain reactions were calculated to be more exergonic than catalyst poisoning pathways. As calculated, preformed enamines generated from the MacMillan imidazolidinone did not displace ethylene from a biscationic (<i>t</i>-Bu)PyBOX-Pt<sup>2+</sup>complex, but neither were the desired C-C bond formations observed under several different conditions.

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