Trost-Ligand

  • 2- diphenylphosphino -N-[ (1R, 2R ) -2 - [(2- diphenylphosphanylbenzoyl ) amino] cyclohexyl] benzamide
  • 2- diphenylphosphino -N-[ (1S, 2S ) -2 - [(2- diphenylphosphanylbenzoyl ) amino] cyclohexyl] benzamide
  • (S, S) -DACH -Trost ligand
  • (R, R) -DACH -Trost ligand

Almost colorless solid

Fixed

136-142 ° C

Template: Infobox chemical / molecular formula search available

The Trost ligand is a chiral tetradentate chelating ligand. It is used for the transition metal Enantioselective synthesis.

It is named after its developer Barry Trost.

Production

The Trost ligand can by amidation of (R, R) - or (S, S) -1,2 -diaminocyclohexane and 2- diphenylphosphinobenzoic acid are produced. The reaction is performed similar to the Steglich esterification conditions. For this purpose, the components are in dichloromethane ( CH2Cl2 ) having dicyclohexylcarbodiimide (DCC) and 4-dimethylaminopyridine (DMAP) were reacted.

Properties

The Trost ligand is a C2-symmetric chiral organic compound. The meso form ( R, S) is achiral. The optical rotation of a one molar solution of the ( S, S) -Trost ligand in methanol at 20 ° C -134 ° at a wavelength of 589 nm

In the complex, the Trost ligand acts as a tetradentate chelating ligand, where he coordinated through two nitrogen-and phosphorus -mediated bonds to the metal center.

Use

The ligand can be used in a number of enantioselective transition metal-catalyzed reactions. A classic application is the Trostsche asymmetric allylic alkylation

CAS registry number Trans-1,2-Diaminocyclohexane N,N'-Dicyclohexylcarbodiimide Tsuji–Trost reaction
784761
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