Palladium-catalyzed asymmetric hydrogenation of 2-aryl cyclic ketones for the synthesis of trans cycloalkanols through dynamic kinetic resolution under acidic conditions

2020 ◽  
Vol 56 (43) ◽  
pp. 5815-5818 ◽  
Author(s):  
Xiang Li ◽  
Zi-Biao Zhao ◽  
Mu-Wang Chen ◽  
Bo Wu ◽  
Han Wang ◽  
...  
Keyword(s):  
Kinetic Resolution ◽  
Asymmetric Hydrogenation ◽  
Dynamic Kinetic Resolution ◽  
Cyclic Ketones ◽  
Palladium Catalyzed ◽  
Acidic Conditions

The first efficient palladium-catalyzed asymmetric hydrogenation of 2-aryl cyclic ketones has been described through dynamic kinetic resolution under acidic conditions, providing a facile access to chiral trans cycloalkanols.

Mechanism and origins of stereo- and enantioselectivities of palladium-catalyzed hydroamination of racemic internal allenes via dynamic kinetic resolution: a computational study

2020 ◽  
Vol 7 (12) ◽  
pp. 1502-1511 ◽  
Author(s):  
Zhenzhen Wu ◽  
Mei Zhang ◽  
Yu Shi ◽  
Genping Huang
Keyword(s):  
Dft Calculations ◽  
Kinetic Resolution ◽  
Computational Study ◽  
Dynamic Kinetic Resolution ◽  
Palladium Catalyzed

DFT calculations were performed to investigate the Pd-catalyzed hydroamination of racemic internal allenes with pyrazoles.

Diastereo- and Enantioselective Asymmetric Hydrogenation of α-Amido-β-keto Phosphonates via Dynamic Kinetic Resolution

2012 ◽  
Vol 15 (1) ◽  
pp. 72-75 ◽  
Author(s):  
Xiaoming Tao ◽  
Wanfang Li ◽  
Xiaoming Li ◽  
Xiaomin Xie ◽  
Zhaoguo Zhang
Keyword(s):  
Kinetic Resolution ◽  
Asymmetric Hydrogenation ◽  
Dynamic Kinetic Resolution

scholarly journals The Silicon–Hydrogen Exchange Reaction: Catalytic Kinetic Resolution of 2-Substituted Cyclic Ketones

Synlett ◽  
2021 ◽  
Author(s):  
Benjamin List ◽  
Hui Zhou ◽  
Pinglu Zhang
Keyword(s):  
Exchange Reaction ◽  
Hydrogen Exchange ◽  
Kinetic Resolution ◽  
Mechanistic Studies ◽  
Dynamic Kinetic Resolution ◽  
Cyclic Ketones ◽  
Silicon Source ◽  
Acid Catalyzed

We have recently reported the strong and confined, chiral acid-catalyzed asymmetric “silicon−hydrogen exchange reaction”. One aspect of this transformation is that it enables access to enantiopure enol silanes in a tautomerizing σ-bond metathesis, via deprotosilylation of ketones with allyl silanes as the silicon source. However, until today, this reaction has not been applied to racemic, 2-substituted, cyclic ketones. We show here that these important substrates readily undergo a highly enantioselective kinetic resolution furnishing the corresponding kinetically preferred enol silanes. Mechanistic studies suggest the fascinating possibility of advancing the process to a dynamic kinetic resolution.

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