Chemoenzymatic synthesis of chiral 4,4'-bipyridyls and their metal-organic frameworks

Chem Commun (Camb). 2008 Nov 21:(43):5538-40. doi: 10.1039/b812366g. Epub 2008 Oct 9.

Abstract

The first enantiopure 4,4'-bipyridyls, , , and have been prepared in four or five steps via bacterial dioxygenase-catalysed cis-dihydroxylation of 4-chloroquinoline and C-C coupling; ligands and are found to be effective building blocks for the preparation of chiral metal-organic frameworks as demonstrated with the rational synthesis of two pillared-grid structures [Zn(2)(fumarate)(2)(L)], which exhibit interesting structural and dynamic aspects.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Catalysis
  • Crystallography, X-Ray
  • Dioxygenases / metabolism*
  • Fumarates / chemistry*
  • Hydroxylation
  • Ligands
  • Models, Molecular
  • Molecular Structure
  • Organometallic Compounds / chemical synthesis*
  • Organometallic Compounds / chemistry
  • Pseudomonas putida / enzymology
  • Pyridines / chemical synthesis*
  • Pyridines / chemistry
  • Pyridines / metabolism*
  • Sphingomonas / enzymology
  • Stereoisomerism
  • Zinc / chemistry*

Substances

  • Fumarates
  • Ligands
  • Organometallic Compounds
  • Pyridines
  • Dioxygenases
  • Zinc
  • 4,4'-bipyridyl