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Amino Acid‐Functionalized Metal‐Organic Frameworks for Asymmetric Base–Metal Catalysis

Rajashree Newar, Naved Akhtar, Neha Antil, Ajay Kumar, Sakshi Shukla, Wahida Begum, Kuntal Manna

2021Angewandte Chemie International Edition91 citationsDOI

Abstract

We report a strategy to develop heterogeneous single-site enantioselective catalysts based on naturally occurring amino acids and earth-abundant metals for eco-friendly asymmetric catalysis. The grafting of amino acids within the pores of a metal-organic framework (MOF), followed by post-synthetic metalation with iron precursor, affords highly active and enantioselective (>99 % ee for 10 examples) catalysts for hydrosilylation and hydroboration of carbonyl compounds. Impressively, the MOF-Fe catalyst displayed high turnover numbers of up to 10 000 and was recycled and reused more than 15 times without diminishing the enantioselectivity. MOF-Fe displayed much higher activity and enantioselectivity than its homogeneous control catalyst, likely due to the formation of robust single-site catalyst in the MOF through site-isolation.

Topics & Concepts

Enantioselective synthesisCatalysisHydroborationHydrosilylationChemistryMetalationMetal-organic frameworkOrganic chemistryHomogeneous catalysisCombinatorial chemistryOrganic synthesisHeterogeneous catalysisAdsorptionMetal-Organic Frameworks: Synthesis and ApplicationsCovalent Organic Framework ApplicationsAsymmetric Hydrogenation and Catalysis
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