CAS 205064-10-4 (+)-1,2-Bis((2S,5S)-2,5-dimethylphospholano)benzene(1,5-cyclooctadiene)rhodium(I) tetrafluoroborate, 98+% (S,S)-Me-DUPHOS-Rh

Synonyms

(+)-1,2-Bis((2S,5S)-2,5-dimethylphospholano)benzene(cyclooctadiene)Rh(I)tetrafluoroborate; (2R,5R)-1-[2-[(2R,5R)-2,5-dimethylphospholan-1-yl]phenyl]-2,5-dimethylphospholane; MFCD01862467; 205064-10-4; AC1MC1E8;

IUPAC Name

cycloocta-1,5-diene;(2S,5S)-1-[2-[(2S,5S)-2,5-dimethylphospholan-1-yl]phenyl]-2,5-dimethylphospholane;rhodium;tetrafluoroborate;

Molecular Weight

604.263g/mol

Molecular Formula

C26H40BF4P2Rh-;

Canonical SMILES

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

InChI

InChI=1S/C18H28P2.C8H12.BF4.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)5;/h5-8,13-16H,9-12H2,1-4H3;1-2,7-8H,3-6H2;;/q;;-1;/t13-,14-,15-,16-;;;/m0.../s1;

InChI Key

ZUMNNKGIZSDCBZ-KXSXXMSISA-N;

Complexity

369

Covalently-Bonded Unit Count

Defined Atom Stereocenter Count

Exact Mass

604.169g/mol

Formal Charge

-1

H-Bond Acceptor

Heavy Atom Count

Monoisotopic Mass

604.169g/mol

Rotatable Bond Count

Topological Polar Surface Area

0A^2

Undefined Bond Stereocenter Count

Application

(+)-1,2-Bis((2S,5S)-2,5-dimethylphospholano)benzene(1,5-cyclooctadiene)rhodium(I) tetrafluoroborate, 98+% (S,S)-Me-DUPHOS-Rh is designed as a highly efficient catalyst for a variety of asymmetric reactions. This product excels in the asymmetric hydrogenation of substituted acetamidoacrylates, enol acetates, tetrasubstituted enamides, and enol phosphonates, delivering products with high enantiomeric excesses. It also forms superior catalysts for asymmetric reductive aminations and provides a novel pathway for enantioselective synthesis of β-amino alcohols and 1,2-diamines. Additionally, it acts as a ligand in the catalytic asymmetric [4+1] cycloaddition of vinylallenes with CO and facilitates the Rh-catalyzed asymmetric enyne cycloisomerization. Furthermore, this product is integral in the catalytic enantioselective addition of dialkylzinc to N-Diphenylphosphinoylimines and plays a key role in palladium-catalyzed asymmetric phosphination, all while being available as an orange or red crystalline powder.

February 22, 2025

Highly Effective Catalyst for Asymmetric Reactions

After using Alfa Chemistry's (+)-1,2-Bis((2S,5S)-2,5-dimethylphospholano)benzene Rh complex, I achieved excellent results in asymmetric hydrogenation. This superior ligand significantly improved enantiomeric excesses in our β-amino alcohol synthesis. Highly recommend for research applications!