Asymmetric ligand

In chemistry a chiral ligand is a specially adapted ligand used for asymmetric synthesis. This ligand is an enantiopure organic compound that combines with a metal center by chelation to form an asymmetric catalyst. This catalyst engages in a chemical reaction and transfers its chirality to the reaction product which as a result also becomes chiral. In an ideal reaction one equivalent of catalyst can turn over many more equivalents of reactant which enables the synthesis of a large amount of a chiral compound from achiral precursors with the aid of a very small (often expensive) chiral ligand.

The first such ligand, the diphosphine DiPAMP was developed in 1968 by William S. Knowles of Monsanto Company, who won the 2001 Nobel Prize in Chemistry, and ultimately used in the industrial production of L-DOPA.

Many thousands of chiral ligands have been prepared and tested since then but only several compound classes have been found to have a general scope. These ligands are therefore called privileged ligands. Important members depicted below are BINOL, BINAP, TADDOL, DIOP, BOX and DuPhos (a phosphine ligand), all available as enantiomeric pairs.

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