Trost ligand

Trost ligand
IUPAC name (1R,2R)-(+)-1,2-diaminocyclohexane-N,N'-bis(2-diphenylphosphinobenzoyl)
Other names Trost's ligand
Identifiers
CAS number	138517-61-0 Y
PubChem	10963521
ChemSpider	9138733 Y
Jmol-3D images	Image 1
SMILES O=C(N[C@H]4CCCC[C@@H]4NC(=O)c3ccccc3P(c1ccccc1)c2ccccc2)c7ccccc7P(c5ccccc5)c6ccccc6
InChI 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 Y Key: AXMSEDAJMGFTLR-ZAQUEYBZSA-N Y 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
Properties
Molecular formula	C44H40N2O2P2
Molar mass	690.75 g/mol
Appearance	white solid
Melting point	136-142 °C
Solubility in water	insoluble; soluble in organic solvents, e.g. acetonitrile, dichloromethane, 1,4-dioxane, methanol, tetrahydrofuran, toluene
Y (verify) (what is: Y/N?) Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa)
Infobox references

The Trost ligand is a chiral ligand pioneered by Barry Trost for use in the palladium-catalyzed Trost asymmetric allylic alkylation. Other C₂-symmetric ligands derived from trans-1,2-diaminocyclohexane (DACH) have also been developed by the Trost group, 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 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)

External links

• Sigma-Aldrich: Trost Ligands
• Trost Research Group