Tetrasubstituted cyclopentadienones as suitable enantiopure ligands with axial chirality

2017 ◽  
Vol 15 (41) ◽  
pp. 8720-8728
Author(s):  
L. Prati ◽  
M. Mancinelli ◽  
A. Ciogli ◽  
A. Mazzanti
Keyword(s):  
Enantioselective Hydrogenation ◽  
Thermally Stable ◽  
Hydrogenation Catalysts ◽  
Axial Chirality

A series of thermally stable atropisomeric phencyclones has been successfully synthesized as ligands in new ruthenium-based enantioselective hydrogenation catalysts.

scholarly journals Computational design of an intramolecular frustrated lewis pair catalyst for enantioselective hydrogenation

2020 ◽  
Vol 19 (02) ◽  
pp. 2050009
Author(s):  
Gitanjali Sharma ◽  
Paul D. Newman ◽  
Rebecca Melen ◽  
James A. Platts
Keyword(s):  
Dft Calculations ◽  
Significant Variation ◽  
Computational Design ◽  
Enantioselective Hydrogenation ◽  
Hybrid Functional ◽  
Hydrogenation Catalysts ◽  
Reaction Barrier ◽  
Lewis Bases ◽  
Frustrated Lewis Pair

We report DFT calculations on potential intramolecular, enantioselective hydrogenation catalysts based around borenium-carbenes based on a camphor scaffold. Using the M06-2X meta-hybrid functional, we find frustrated Lewis pair (FLP) behavior with suitably chosen linkers that prevent association of Lewis bases with the borenium center. These intramolecular FLPs are predicted to be able to heterolytically dissociate H2. Barriers to dissociation and the endo/exoergic nature of the reaction can be tuned by the nature of the base and substituent on B. The reactivity of the hydrogenated FLP catalyst with olefin and carbonyl substrates is then explored: we predict concerted reactions for all substrates considered with relatively low barriers and large exoergic character. Hydrogenation of both faces of a prochiral substrate is also examined, indicating a small but significant variation in reaction barrier in favor of the Si-face, ascribed to stronger interactions with the aromatic [Formula: see text]-system in the TS compared to the Re-face.

Enantioselective hydrogenation of cyclic imines catalysed by Noyori–Ikariya half-sandwich complexes and their analogues

2016 ◽  
Vol 52 (2) ◽  
pp. 362-365 ◽  
Author(s):  
B. Vilhanová ◽  
J. Václavík ◽  
P. Šot ◽  
J. Pecháček ◽  
J. Zápal ◽  
...  
Keyword(s):  
Trifluoroacetic Acid ◽  
Asymmetric Hydrogenation ◽  
Enantioselective Hydrogenation ◽  
Transfer Hydrogenation ◽  
Sandwich Complexes ◽  
Hydrogenation Catalysts ◽  
Half Sandwich

Trifluoroacetic acid activates cyclic imines in a new non-air sensitive asymmetric hydrogenation method. New transfer hydrogenation catalysts are demonstrated.

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