Consolation ligand

from Wikipedia, the free encyclopedia
Structural formula
Structure of the (R, R) -rost ligand
( R , R ) -DACH-Trost ligand
General
Surname Consolation ligand
other names
  • 2-Diphenylphosphanyl- N - {(1 R , 2 R ) -2 - [(2-diphenylphosphanylbenzoyl) amino] cyclohexyl} benzamide
  • 2-Diphenylphosphanyl- N - {(1 S , 2 S ) -2 - [(2-diphenylphosphanylbenzoyl) amino] cyclohexyl} benzamide
  • ( S , S ) -DACH-Trost ligand
  • ( R , R ) -DACH-Trost ligand
Molecular formula C 44 H 40 N 2 O 2 P 2
Brief description

almost colorless solid

External identifiers / databases
CAS number
  • 138517-61-0 [( R , R ) -enantiomer]
  • 169689-05-8 [( S , S ) -enantiomer]
PubChem 10963521
ChemSpider 9138733
Wikidata Q200998
properties
Molar mass 690.75 g mol −1
Physical state

firmly

Melting point

136-142 ° C

safety instructions
GHS labeling of hazardous substances
no GHS pictograms
H and P phrases H: no H-phrases
P: no P-phrases
As far as possible and customary, SI units are used. Unless otherwise noted, the data given apply to standard conditions .

The consolation ligand is a chiral tetradentate chelating ligand . It is used for transition metal catalyzed enantioselective synthesis .

It is named after its developer Barry Trost .

Manufacturing

The Trost ligand can be produced by amidation from ( R , R ) - or ( S , S ) - 1,2-diaminocyclohexane and 2-diphenylphosphinobenzoic acid. The reaction is carried out under conditions similar to the Steglich esterification . For this purpose, the components are reacted in dichloromethane (CH 2 Cl 2 ) with dicyclohexylcarbodiimide (DCC) and 4-dimethylaminopyridine (DMAP).

Synthesis of the Trost ligand

properties

The Trost ligand is a C 2 -symmetrical chiral organic compound . The meso form ( R , S ) is achiral. The rotation value of a one-molar solution of the ( S , S ) -rost ligand in methanol at 20 ° C. is −134 ° at a wavelength of 589 nm .

In the complex , the Trost ligand acts as a tetradentate chelate ligand, coordinating via two nitrogen and two phosphorus- mediated bonds at the metal center .

use

The ligand can be used in a variety of enantioselective transition metal catalyzed reactions. A classic area of ​​application is Trost's asymmetric allylic alkylation .

Individual evidence

  1. ↑ a b c d data sheet (S, S) -DACH-phenyl Trost ligand from Sigma-Aldrich , accessed on May 29, 2011 ( PDF ).
  2. ↑ Doctoral thesis BJ Lüssem RWTH Aachen.

literature