Biomimetic Reductive Amination of Fluoro Aldehydes and Ketonesvia[1,3]-Proton Shift Reaction.1Scope and Limitations

1996 ◽  
Vol 61 (19) ◽  
pp. 6563-6569 ◽  
Author(s):  
Taizo Ono ◽  
Valery P. Kukhar ◽  
Vadim A. Soloshonok
Keyword(s):  
Reductive Amination ◽  
Proton Shift ◽  
Shift Reaction

Catalytic asymmetric synthesis of β-fluoroalkyl-β-amino acids via biomimetic [1,3]-proton shift reaction

1994 ◽  
Vol 35 (28) ◽  
pp. 5063-5064 ◽  
Author(s):  
Vadim A. Soloshonok ◽  
Alexander G. Kirilenko ◽  
Sergey V. Galushko ◽  
Valery P. Kukhar
Keyword(s):  
Amino Acids ◽  
Asymmetric Synthesis ◽  
Proton Shift ◽  
Catalytic Asymmetric Synthesis ◽  
Catalytic Asymmetric ◽  
Shift Reaction

Chiral Zinc(II)-Catalyzed Enantioselective Tandem α-Alkenyl Addition/Proton Shift Reaction of Silyl Enol Ethers with Ketimines

2019 ◽  
Vol 131 (8) ◽  
pp. 2486-2490 ◽  
Author(s):  
Tengfei Kang ◽  
Weidi Cao ◽  
Liuzhen Hou ◽  
Qiong Tang ◽  
Sijia Zou ◽  
...  
Keyword(s):  
Enol Ethers ◽  
Silyl Enol Ethers ◽  
Proton Shift ◽  
Shift Reaction

A practical route to fluoroalkyl- and fluoroarylamines by base-catalyzed [1,3]-proton shift reaction

1994 ◽  
Vol 35 (19) ◽  
pp. 3119-3122 ◽  
Author(s):  
Vadim A. Soloshonok ◽  
Alexander G. Kirilenko ◽  
Valery P. Kukhar ◽  
Giuseppe Resnati
Keyword(s):  
Proton Shift ◽  
Shift Reaction

Some Aspects of Reductive Amination in the Presence of Carbon Monoxide: Cyclopropyl Ketones as Bifunctional Electrophiles

Synthesis ◽  
2017 ◽  
Vol 49 (12) ◽  
pp. 2640-2651 ◽  
Author(s):  
Oleg Afanasyev ◽  
Alexey Tsygankov ◽  
Dmitry Usanov ◽  
Dmitry Perekalin ◽  
Alexandra Samoylova ◽  
...  
Keyword(s):  
Reductive Amination ◽  
Reaction Pathway ◽  
Water Source ◽  
Water Gas Shift ◽  
Water Gas Shift Reaction ◽  
Rhodium Catalysis ◽  
Multiple Factors ◽  
Shift Reaction ◽  
Cyclopropyl Ketones ◽  
Water Gas

We conducted detailed studies on CO-assisted reductive chemistry with cyclopropyl ketones as a special type of substrate. Multiple factors influencing the outcome of the reaction have been studied for both ruthenium and rhodium catalysis. An unusual rearrangement of aminomethylcyclopropanes was found. We showed that some reductive reactions, which were believed to proceed through a water–gas shift reaction pathway, can nonetheless take place even without an external or internal water source, indicating a more interesting reaction mechanism. Cyclopropylketones were employed as bifunctional electrophiles and, depending on the conditions, the reaction with an amine can lead to a number of products, including aminoketones, cyclopropyl methylamines, pyrrolidines or 1,4-diaminopentanes.

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