(-)-1,2-BIS((2R,5R)-2,5-DIETHYLPHOSPHOLANO)BENZENE(CYCLOOCTADIENE)RHODIUM(I)TRIFLUOROMETHANESULFONATE

Chemical Properties

storage temp.	Refrigerator (+4°C)
form	crystal
color	orange
Sensitive	Air Sensitive
Exposure limits	ACGIH: TWA 1 mg/m3 NIOSH: IDLH 100 mg/m3; TWA 0.1 mg/m3
InChIKey	HZLILTNLWVOBFS-KYOOHHHUSA-M
SMILES	[Rh+].[O-]S(=O)(=O)C(F)(F)F.C1CC=CCCC=C1.CC[C@@H]2CC[C@@H](CC)P2c3ccccc3P4[C@H](CC)CC[C@H]4CC

Provider	Language
ACROS	English

Reaction

The DUPHOS family of catalysts is highly efficient for the asymmetric hydrogenation of various substituted acetamidoacrylates and enol acetates yielding products of high enantiomeric excesses. Efficient ligand for the asymmetric hydrogenation of tetrasubstituted enamides.
Forms superior catalysts for asymmetric reductive aminations.
Catalyst used for the asymmetric hydrogenation of enol phosphonates.
A novel enantioselective synthesis of β-amino alcohols and 1,2-diamines.
Ligand for the catalytic asymmetric [4+1] cycloaddition of vinylallenes with CO.
Ligand for the Rh-catalyzed asymmetric enyne cycloisomerization.
Catalytic enantioselective addition of dialkylzinc to N-Diphenylphosphinoylimines.
Palladium catalyzed asymmetric phosphination.

Chemical Properties

orange to orange-brown crystals

Uses

Stereoselective synthesis of δ-amino acid derivatives via asymmetric hydrogenation of acetylaminopentenoic acid derivatives
Stereoselective synthesis of manzacidins A and C via stereoselective hydrogenation
Stereoselective synthesis of tetracyclic core of manzamine A via Rh-catalyzed asymmetric hydrogenation, diastereoselective Diels-Alder reaction, Eschenmoser-Tanabe fragmentation, Chang′s amide formation, and Hofmann rearrangement
Asymmetric preparation of chiral Cbz-aminodifluorobutyric acid Me ester and its analogs
Biphasic catalytic hydrogenations in ionic liquids with addition of water as a second solvent
Preparation of cyclobutane-containing amino acids via asymmetric hydrogenations of cyclobutyl enamides
Asymmetric preparation of both enantiomers of (dimethoxycoumaryl)alanine as suitable fluorescent peptide labels

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