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Trost ligand information


Trost ligand
Names
IUPAC name
(1R,2R)-(+)-1,2-diaminocyclohexane-N,N'-bis(2-diphenylphosphinobenzoyl) [citation needed]
Preferred IUPAC name
N,N′-[(1R,2R)-cyclohexane-1,2-diyl]bis[2-(diphenylphosphanyl)benzamide]
Other names
Trost's ligand
Identifiers
CAS Number
  • 138517-61-0 ☒N
3D model (JSmol)
  • Interactive image
ChemSpider
  • 9138733 checkY
PubChem CID
  • 10963521
UNII
  • M4RRX95R5F checkY
CompTox Dashboard (EPA)
  • DTXSID80894121 Edit this at Wikidata
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 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
SMILES
  • O=C(N[C@H]4CCCC[C@@H]4NC(=O)c3ccccc3P(c1ccccc1)c2ccccc2)c7ccccc7P(c5ccccc5)c6ccccc6
Properties
Chemical formula
 C44H40N2O2P2
Molar mass 690.75 g/mol
Appearance White solid
Melting point 136 to 142 °C (277 to 288 °F; 409 to 415 K)
Solubility in water
 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).
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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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Trost ligand

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The Trost ligand is a diphosphine used in the palladium-catalyzed Trost asymmetric allylic alkylation. Other C2-symmetric ligands derived from trans-1...

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Barry Trost

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University. The Tsuji-Trost reaction and the Trost ligand are named after him. He is prominent for advancing the concept of atom economy. Trost was born in Philadelphia...

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Trost

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firm Trost asymmetric allylic alkylation, a chemical reaction developed by Barry Trost Trost ligand, a chemical ligand designed by Barry Trost Trost ("Consolation")...

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Tetradentate ligand

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complexes. This arrangement is illustrated by complexes of the Trost ligand. The ligand can bend so that one donor atom is at the pole and the remaining...

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Galantamine total synthesis

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carbonate, 2days c Troc-Cl, DMAP, Pyridine, dichloromethane d palladium, Trost ligand, triethylamine, dichloromethane e 1.5 mol % TsOH, CH(OMe)3, methanol...

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Carroll rearrangement

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rearrangement is catalyzed by tris(dibenzylideneacetone)dipalladium(0) and the Trost ligand: A similar reaction uses additional naphthol. This reaction delivers...

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oxazoline based ligands (S)-iPr-PHOX - A specific PHOX ligand Bisoxazolines (BOX) Trisoxazolines (TRISOX) Structurally related ligands Trost ligand Diphenyl-2-pyridylphosphine...

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Vinylidene group

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Vinylene group, −CH=CH− Methylene group, −CH2− Vinyl group, −CH=CH2 Barry M. Trost; Andrew McClory "Metal Vinylidenes as Catalytic Species in Organic Reactions"...

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Organoaluminium chemistry

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accommodates four carbon ligands. The triorganoaluminium compounds are thus usually dimeric with a pair of bridging alkyl ligands, e.g., Al2(C2H5)4(μ-C2H5)2...

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Organopalladium chemistry

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halogenide with an olefin. Pd(0) intermediates are implicated. 1973 - The Trost asymmetric allylic alkylation is a nucleophilic substitution. 1975 - The...

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Benzyl group

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Organic Chemistry. 49 (1): 51–56. doi:10.1021/jo00175a010. ISSN 0022-3263. Trost, Barry M.; Waser, Jerome; Meyer, Arndt (2007-11-01). "Total Synthesis of...

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Picrotoxin

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(26): 11376–11381. doi:10.1021/jacs.0c05042. PMC 8011636. PMID 32573211. Trost B, Krische MJ (1996). "Picrotoxinin". Journal of the American Chemical Society...

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Lewis acid catalysis

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Lewis Acid Carbonyl Complexation, in Comprehensive Organic Synthesis, Trost, B.M.; Fleming, I., Eds. Pergamon, Oxford, 1991, vol. 1, chap. 1.10, pp...

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cyclobutadieneiron tricarbonyl pointed to the possibility complexes of other organic ligands that are elusive in their free state. Trimethylenemethane (TMM) has a natural...

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Sterimol parameter

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groups of Rice, Evans, Fuchs, Parker, Overman, Mulzer-Trauner, White, Taber, Trost, Fukuyama, Guillou, and Stork. Because of the stereochemical complexity...

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Trimethylenemethane

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Journal of the Chemical Society D (21): 1419–1420. doi:10.1039/C29700001419. Trost Barry M (1979). "New conjunctive reagents. 2-Acetoxymethyl-3-allyltrimethylsilane...

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Dimethylformamide

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of organometallic compounds, it is used as a source of carbon monoxide ligands. DMF is a common solvent used in electrospinning. DMF is commonly used...

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