CAS 187682-63-9 (-)-1,2-Bis((2R,5R)-2,5-dimethylphospholano)benzene(1,5-cyclooctadiene)rhodium(I)trifluoromethanesulfonate, 98+% (R,R)-Me-DUPHOS-Rh

Synonyms

187682-63-9;1,2-Bis[(2R,5R)-2,5-dimethylphospholano]benzene(cyclooctadiene)rhodium(I) trifluoromethanesulfonate;136705-75-4;MFCD00269862;DTXSID50450298;J-012077;(-)-1,2-Bis((2R,5R)-2,5-dimethylphospholano)benzene(cyclooctadiene)rhodium(I) trifluoromethanesulfonate;1,2-Bis[(2R,5R)-2,5-dimethylphospholano]benzene(cyclooctadiene)rhodium(I) trifluoromethanesulfonate, >=97%;

IUPAC Name

(1Z,5Z)-cycloocta-1,5-diene;(2R,5R)-1-[2-[(2R,5R)-2,5-dimethylphospholan-1-yl]phenyl]-2,5-dimethylphospholane;rhodium;trifluoromethanesulfonate;

Molecular Weight

666.522g/mol

Molecular Formula

C27H40F3O3P2RhS-;

Canonical SMILES

CC1CCC(P1C2=CC=CC=C2P3C(CCC3C)C)C.C1CC=CCCC=C1.C(F)(F)(F)S(=O)(=O)[O-].[Rh];

InChI

InChI=1S/C18H28P2.C8H12.CHF3O3S.Rh/c1-13-9-10-14(2)19(13)17-7-5-6-8-18(17)20-15(3)11-12-16(20)4;1-2-4-6-8-7-5-3-1;2-1(3,4)8(5,6)7;/h5-8,13-16H,9-12H2,1-4H3;1-2,7-8H,3-6H2;(H,5,6,7);/p-1/b;2-1-,8-7-;;/t13-,14-,15-,16-;;;/m1.../s1;

InChI Key

HFNBCEIZBZROGX-MYDVBLLJSA-M;

Complexity

495

Covalently-Bonded Unit Count

Defined Atom Stereocenter Count

Defined Bond Stereocenter Count

Exact Mass

666.118g/mol

Formal Charge

-1

H-Bond Acceptor

Heavy Atom Count

Monoisotopic Mass

666.118g/mol

Rotatable Bond Count

Topological Polar Surface Area

65.6A^2

Application

The product, (-)-1,2-Bis((2R,5R)-2,5-dimethylphospholano)benzene(1,5-cyclooctadiene)rhodium(I)trifluoromethanesulfonate, 98+% (R,R)-Me-DUPHOS-Rh, appears as an orange to orange-brown crystalline powder and serves as a versatile catalyst within the DUPHOS family. It is primarily used for the asymmetric hydrogenation of a wide range of compounds, including substituted acetamidoacrylates, enol acetates, and tetrasubstituted enamides, resulting in products with high enantiomeric excesses. Additionally, it effectively forms superior catalysts for asymmetric reductive aminations and hydrogenation of enol phosphonates. This compound also plays a crucial role in novel enantioselective syntheses of β-amino alcohols and 1,2-diamines. As a ligand, it aids in catalytic asymmetric [4+1] cycloadditions of vinylallenes with carbon monoxide, Rh-catalyzed asymmetric enyne cycloisomerizations, and the enantioselective addition of dialkylzinc to N-Diphenylphosphinoylimines. Furthermore, it is employed in palladium catalyzed asymmetric phosphination.

February 21, 2025

Highly Efficient Catalyst for Asymmetric Hydrogenation

I've used Alfa Chemistry's (R,R)-Me-DUPHOS-Rh in asymmetric hydrogenation research. This orange-brown powder excelled in producing high enantiomeric excess substrates, particularly with acetamidoacrylates and enol phosphonates. Impressive results!