A homochiral porous metal-organic framework for highly enantioselective heterogeneous asymmetric catalysis

J Am Chem Soc. 2005 Jun 29;127(25):8940-1. doi: 10.1021/ja052431t.

Abstract

A homochiral porous noninterpenetrating metal-organic framework (MOF), 1, was constructed by linking infinite 1D [Cd(mu-Cl)2]n zigzag chains with axially chiral bipyridine bridging ligands containing orthogonal secondary functional groups. The secondary chiral dihydroxy groups accessible via the large open channels in 1 were utilized to generate a heterogeneous asymmetric catalyst for the addition of diethyzinc to aromatic aldehydes to afford chiral secondary alcohols at up to 93% enantiomeric excess (ee). Control experiments with dendritic aromatic aldehydes of different sizes indicate that the heterogeneous asymmetric catalyst derived from 1 is both highly active and enantioselective as a result of the creation of readily accessible, uniform active catalyst sites inside the porous MOF.

Publication types

  • Research Support, Non-U.S. Gov't
  • Research Support, U.S. Gov't, Non-P.H.S.

MeSH terms

  • Aldehydes / chemical synthesis
  • Aldehydes / chemistry
  • Catalysis
  • Crystallography, X-Ray
  • Hydrogen Bonding
  • Ligands
  • Models, Molecular
  • Molecular Structure
  • Organometallic Compounds / chemistry*
  • Porosity
  • Stereoisomerism
  • Titanium / chemistry*

Substances

  • Aldehydes
  • Ligands
  • Organometallic Compounds
  • Titanium