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Issue 8, 2012
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Cavity-induced enantioselectivity reversal in a chiral metal–organic framework Brønsted acid catalyst

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Abstract

A pair of highly porous chiral metal–organic frameworks (CMOFs 1 and 2) were constructed from [Cu2(carboxylate)4] secondary building units (SBUs) and chiral 3,3′,6,6′- or 4,4′,6,6′-tetra(benzoate) ligands derived from 1,1′-binaphthyl-2,2′-phosphoric acid. Both 1 and 2 were active catalysts for Friedel–Crafts reactions between indole and imines. Interestingly, the 1-catalyzed asymmetric reactions yielded the major enantiomers of the opposite chirality to those afforded by the corresponding homogeneous catalyst. Structural analyses and QM/MM calculations revealed that the flip of product handedness results from the chiral environment of CMOF-1 cavity, similar to enzymatic catalysis in which the product stereoselectivity is determined by the enzyme pocket.

Graphical abstract: Cavity-induced enantioselectivity reversal in a chiral metal–organic framework Brønsted acid catalyst

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Publication details

The article was received on 27 Mar 2012, accepted on 04 May 2012 and first published on 04 May 2012


Article type: Edge Article
DOI: 10.1039/C2SC20379K
Citation: Chem. Sci., 2012,3, 2623-2627
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    Cavity-induced enantioselectivity reversal in a chiral metal–organic framework Brønsted acid catalyst

    M. Zheng, Y. Liu, C. Wang, S. Liu and W. Lin, Chem. Sci., 2012, 3, 2623
    DOI: 10.1039/C2SC20379K

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