CAS 136705-77-6 (-)-1,2-Bis((2R,5R)-2,5-diethylphospholano)benzene(1,5-cyclooctadiene)rhodium(I) trifluoromethanesulfonate, 98+% (R,R)-Et-DUPHOS-Rh

Synonyms

(-)-1,2-Bis((2R,5R)-2,5-diethylphospholano)benzene(cyclooctadiene)rhodium(I) trifluoromethanesulfonate; 1,2-Bis[(2R,5R)-2,5-diethylphospholano]benzene(1,5-cyclooctadiene)rhodium(I) trifluoromethanesulfonate; MFCD18909711; 136705-77-6; J-006893;

IUPAC Name

(1Z,5Z)-cycloocta-1,5-diene;(2R,5R)-1-[2-[(2R,5R)-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-;;;/m1.../s1;

InChI Key

XGPXBCKGQLCHDW-KYOOHHHUSA-M;

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((2R,5R)-2,5-diethylphospholano)benzene(1,5-cyclooctadiene)rhodium(I) trifluoromethanesulfonate, 98+% (R,R)-Et-DUPHOS-Rh is to serve as a highly efficient catalyst for various stereoselective and asymmetric synthetic transformations. This catalyst is particularly valuable in the synthesis of δ-amino acid derivatives, manzacidins A and C, and the tetracyclic core of manzamine A through stereoselective and asymmetric hydrogenation processes. It also facilitates the preparation of chiral Cbz-aminodifluorobutyric acid ester and other analogs, and is effective in biphasic catalytic hydrogenations in ionic liquids. Additionally, it aids in the creation of cyclobutane-containing amino acids, serves in the synthesis of both enantiomers of (dimethoxycoumaryl)alanine, and is instrumental for the asymmetric hydrogenation of substituted acetamidoacrylates, enol acetates, tetrasubstituted enamides, and enol phosphonates. The catalyst also forms superior systems for asymmetric reductive aminations, the enantioselective synthesis of β-amino alcohols and 1,2-diamines, catalytic asymmetric cycloaddition of vinylallenes with CO, Rh-catalyzed enyne cycloisomerization, enantioselective addition of dialkylzinc to N-Diphenylphosphinoylimines, and palladium-catalyzed asymmetric phosphination.

January 13, 2025

Outstanding Catalyst for Asymmetric Synthesis

Using Alfa Chemistry's (-)-1,2-Bis((2R,5R)-2,5-diethylphospholano)benzene catalyst facilitated remarkable enantiomeric excess in hydrogenation. An indispensable tool for efficient asymmetric reactions in my research, providing consistent and high-quality results.