Synthetic and computational assessment of a chiral metal-organic framework catalyst for predictive asymmetric transformation.

Chemical Science
Jérôme CanivetCaroline Mellot-Draznieks

Abstract

Understanding and controlling molecular recognition mechanisms at a chiral solid interface is a continuously addressed challenge in heterogeneous catalysis. Here, the molecular recognition of a chiral peptide-functionalized metal-organic framework (MOF) catalyst towards a pro-chiral substrate is evaluated experimentally and in silico. The MIL-101 metal-organic framework is used as a macroligand for hosting a Noyori-type chiral ruthenium molecular catalyst, namely (benzene)Ru@MIL-101-NH-Gly-Pro. Its catalytic perfomance toward the asymmetric transfer hydrogenation (ATH) of acetophenone into R- and S-phenylethanol are assessed. The excellent match between the experimentally obtained enantiomeric excesses and the computational outcomes provides a robust atomic-level rationale for the observed product selectivities. The unprecedented role of the MOF in confining the molecular Ru-catalyst and in determining the access of the prochiral substrate to the active site is revealed in terms of highly face-specific host-guest interactions. The predicted surface-specific face differentiation of the prochiral substrate is experimentally corroborated since a three-fold increase in enantiomeric excess is obtained with the heterogeneous MOF-base...Continue Reading

References

Apr 20, 2005·Accounts of Chemical Research·Gérard FéreyFranck Millange
Jun 28, 2006·Angewandte Chemie·Maja HeitbaumIris Escher
Oct 4, 2011·Chemical Communications : Chem Comm·Jerome CanivetDavid Farrusseng
Mar 9, 2013·Journal of the American Chemical Society·Jerome CanivetDavid Farrusseng
Mar 26, 2015·Nature Communications·Depeng ZhaoBen L Feringa
Jun 30, 2015·Journal of the American Chemical Society·Jonathan BonnefoyDavid Farrusseng
Nov 1, 2016·Nature Materials·Allegra A LatimerJens K Nørskov
Nov 3, 2016·Chemistry : a European Journal·Tanya K TodorovaCaroline Mellot-Draznieks

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