Trost ligand

Trost ligand
Names
IUPAC name
(1R,2R)-(+)-1,2-diaminocyclohexane-N,N'-bis(2-diphenylphosphinobenzoyl)
Preferred IUPAC name
N,N′-[(1R,2R)-cyclohexane-1,2-diyl]bis[2-(diphenylphosphanyl)benzamide]
Other names
Trost's ligand
Identifiers
3D model (JSmol)
ChemSpider
UNII
  • InChI=1S/C44H40N2O2P2/c47-43(37-27-13-17-31-41(37)49(33-19-5-1-6-20-33)34-21-7-2-8-22-34)45-39-29-15-16-30-40(39)46-44(48)38-28-14-18-32-42(38)50(35-23-9-3-10-24-35)36-25-11-4-12-26-36/h1-14,17-28,31-32,39-40H,15-16,29-30H2,(H,45,47)(H,46,48)/t39-,40-/m0/s1 checkY
    Key: AXMSEDAJMGFTLR-ZAQUEYBZSA-N checkY
  • InChI=1/C44H40N2O2P2/c47-43(37-27-13-17-31-41(37)49(33-19-5-1-6-20-33)34-21-7-2-8-22-34)45-39-29-15-16-30-40(39)46-44(48)38-28-14-18-32-42(38)50(35-23-9-3-10-24-35)36-25-11-4-12-26-36/h1-14,17-28,31-32,39-40H,15-16,29-30H2,(H,45,47)(H,46,48)/t39-,40-/m0/s1
    Key: AXMSEDAJMGFTLR-ZAQUEYBZBE
  • O=C(N[C@H]4CCCC[C@@H]4NC(=O)c3ccccc3P(c1ccccc1)c2ccccc2)c7ccccc7P(c5ccccc5)c6ccccc6
Properties
C44H40N2O2P2
Molar mass 690.75 g/mol
Appearance White solid
Melting point 136 to 142 °C (277 to 288 °F; 409 to 415 K)
Insoluble; soluble in organic solvents (e.g. acetonitrile, dichloromethane) 1,4-dioxane, methanol, tetrahydrofuran, toluene
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
☒N verify (what is checkY☒N ?)
Infobox references

The Trost ligand is a diphosphine used in the palladium-catalyzed Trost asymmetric allylic alkylation. Other C2-symmetric ligands derived from trans-1,2-diaminocyclohexane (DACH) have been developed, such as the (R,R)-DACH-naphthyl ligand derived from 2-diphenylphosphino-1-naphthalenecarboxylic acid. Related bidentate phosphine-containing ligands derived from other chiral diamines and 2-diphenylphosphinobenzoic acid have also been developed for applications in asymmetric synthesis.

(R,R)-DACH-naphthyl Trost ligand, (1R,2R)-(+)-1,2-diaminocyclohexane-N,N′-bis(2-diphenylphosphino-1-naphthoyl)


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