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Updated: Oct 16, 2026

Development of Heterogeneous Enantioselective Catalysts using Chiral Metal-Organic Frameworks (MOFs)
Published on: January 17, 2020
Novel binuclear chiral zirconium catalysts used in enantioselective strecker reactions
1Graduate School of Pharmaceutical Sciences, The University of Tokyo, CREST, Japan Science and Technology Corporation (JST), Tokyo, Japan. skobayas@mol.f.u-tokyo.ac.jp
Abstract:
A novel binuclear chiral zirconium catalyst was successfully used in enantioselective Strecker reactions. The catalyst was readily prepared from zirconium t-butoxide (Zr(OtBu)4), (R)-6,6'-dibromo-1, 1'-bi-2-naphthol ((R)-6-Br-BINOL), and (R)-3,3'-dibromo-1, 1'-bi-2-naphthol ((R)-3-Br-BINOL) to form unique binuclear structure. It was revealed that a combination of (R)-6-Br-BINOL and (R)-3-Br-BINOL was essential in these asymmetric reactions and that much lower selectivities were obtained by using other combinations. Two-component (an imine and hydrogen cyanide (HCN)) and three-component (an aldehyde, an amine, and HCN) Strecker reactions proceeded smoothly in the presence of a catalytic amount of the chiral zirconium catalyst to afford the corresponding alpha-amino nitrile derivatives in high yields with high enantioselectivities.
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