Journal
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
Volume 58, Issue 41, Pages 14748-14757Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/anie.201908959
Keywords
asymmetric catalysis; Bronsted acids; metal-organic frameworks; phosphoric acid; porosity
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Funding
- National Science Foundation of China [21522104, 21620102001, 21875136, 91856204]
- National Key Basic Research Program of China [2016YFA0203400]
- Key Project of Basic Research of Shanghai [17JC1403100, 18JC1413200]
- Shanghai Rising-Star Program [19QA1404300]
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Chiral phosphoric acids are incorporated into indium-based metal-organic frameworks (In-MOFs) by sterically preventing them from coordination. This concept leads to the synthesis of three chiral porous 3D In-MOFs with different network topologies constructed from three enantiopure 1,1 '-biphenol-phosphoric acid derived tetracarboxylate linkers. More importantly, all the uncoordinated phosphoric acid groups are periodically aligned within the channels and display significantly enhanced acidity compared to the non-immobilized acids. This facilitates the Bronsted acid catalysis of asymmetric condensation/amine addition and imine reduction. The enantioselectivities can be tuned (up to >99 % ee) by varying the substituents to achieve a nearly linear correlation with the concentrations of steric bulky groups in the MOFs. DFT calculations suggest that the framework provides a chiral confined microenvironment that dictates both selectivity and reactivity of chiral MOFs.
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