Journal
ADVANCED SYNTHESIS & CATALYSIS
Volume 363, Issue 11, Pages 2861-2865Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/adsc.202001536
Keywords
Kinetic Resolution; Asymmetric Hydrogenation; Planar Chirality; [2; 2]Paracyclophane
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Funding
- Deutsche Forschungsgemeinschaft under Germany's Excellence Strategy [3DMM2O-EXC-2082/1-390761711]
- DFG [TRR 88/3MET]
- Projekt DEAL
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A kinetic resolution method was developed to obtain enantiomerically pure PCP derivatives through ruthenium-catalyzed enantioselective hydrogenation, providing important intermediates for the synthesis of chiral materials and catalysts.
[2.2]Paracyclophane (PCP) derivatives have been promising platforms to study the element of planar chirality and through-space electronic communications in pi-stacked molecular systems. To access enantiomerically pure derivatives thereof, a kinetic resolution of 4-acetyl[2.2]-PCP employing a ruthenium-catalyzed enantioselective hydrogenation process was developed. This method can be performed on a multigram-scale and gives access to enantiomerically pure derivatives with planar and central chirality of (R-p)-4-acetyl-PCP (>= 97% ee, 43%) and (Sp,S)-PCP derivatives (>= 97% ee, 46%), which are useful intermediates for the synthesis of sterically demanding PCP-based ligand/catalyst systems and chiral synthons for engineering cyclophane-based chiroptical materials.
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