CAS 142184-30-3 (+)-1,2-Bis((2S,5S)-2,5-diethylphospholano)benzene(1,5-cyclooctadiene)rhodium(I) trifluoromethanesulfonate, 98+% (S,S)-Et-DUPHOS-Rh

Synonyms

1,2-Bis[(2S,5S)-2,5-diethylphospholano]benzene(1,5-cyclooctadiene)rhodium(I) trifluoromethanesulfonate; (+)-1,2-Bis((2S,5S)-2,5-diethylphospholano)benzene(1,5-cyclooctadiene)rhodium(I) trifluoromethanesulfonate; AKOS032947597; 1,2-bis[(2S,5S)-2,5-diethyl-phospholano]benzene(1,5-cyclooctadiene)rhodium(I) trifluoromethanesulfonate; MFCD00269861; SC-21592;

IUPAC Name

(1Z,5Z)-cycloocta-1,5-diene;(2S,5S)-1-[2-[(2S,5S)-2,5-diethylphospholan-1-yl]phenyl]-2,5-diethylphospholane;rhodium;trifluoromethanesulfonate;

Molecular Weight

722.63g/mol

Molecular Formula

C31H48F3O3P2RhS-;

Canonical SMILES

CCC1CCC(P1C2=CC=CC=C2P3C(CCC3CC)CC)CC.C1CC=CCCC=C1.C(F)(F)(F)S(=O)(=O)[O-].[Rh];

InChI

InChI=1S/C22H36P2.C8H12.CHF3O3S.Rh/c1-5-17-13-14-18(6-2)23(17)21-11-9-10-12-22(21)24-19(7-3)15-16-20(24)8-4;1-2-4-6-8-7-5-3-1;2-1(3,4)8(5,6)7;/h9-12,17-20H,5-8,13-16H2,1-4H3;1-2,7-8H,3-6H2;(H,5,6,7);/p-1/b;2-1-,8-7-;;/t17-,18-,19-,20-;;;/m0.../s1;

InChI Key

XGPXBCKGQLCHDW-ZCTOJWETSA-M;

Storage

Refrigerator (+4°C)

Complexity

539

Covalently-Bonded Unit Count

Defined Atom Stereocenter Count

Defined Bond Stereocenter Count

Exact Mass

722.181g/mol

Formal Charge

-1

H-Bond Acceptor

Heavy Atom Count

Monoisotopic Mass

722.181g/mol

Rotatable Bond Count

Topological Polar Surface Area

65.6A^2

Application

The purpose of (+)-1,2-Bis((2S,5S)-2,5-diethylphospholano)benzene(1,5-cyclooctadiene)rhodium(I) trifluoromethanesulfonate, or (S,S)-Et-DUPHOS-Rh, is to serve as a highly efficient catalyst in various enantioselective reactions, particularly in the synthesis of (S)-2-quinolylalanine via asymmetric hydrogenation. As an electron-rich C2 symmetric bis(phospholane) ligand, it excels in asymmetric hydrogenations of diverse substrates like substituted acetamidoacrylates and enol acetates, yielding products with high enantiomeric excesses. Additionally, it is an effective ligand in processes such as asymmetric reductive aminations, enyne cycloisomerizations, catalytic syntheses of β-amino alcohols and 1,2-diamines, and the [4+1] cycloaddition of vinylallenes with CO. It further supports catalytic enantioselective additions of dialkylzinc to N-diphenylphosphinoylimines and palladium-catalyzed asymmetric phosphination, making it a versatile tool in the field of synthetic organic chemistry.

January 29, 2025

Exceptional Catalyst for Asymmetric Synthesis

We used (S,S)-Et-DUPHOS-Rh as a catalyst in our lab for enantioselective synthesis. It consistently delivered high enantiomeric excesses, particularly with tetrasubstituted enamides. The orange-red crystals were easy to handle and very effective.