CAS 210057-23-1 (-)-1,2-Bis((2R,5R)-2,5-dimethylphospholano)benzene(1,5-cyclooctadiene)rhodium(I) tetrafluoroborate, 98+% (R,R)-Me-DUPHOS-Rh

Synonyms

210057-23-1;MFCD01862466;057B231;(-)-1,2-Bis[(2R,5R)-dimethylphospholano]benzene(cyclooCtadiene)rhodium(I) tetrafluoroborate;1,2-Bis[(2R,5R)-2,5-dimethylphospholano]benzene(cyclooctadiene)rhodium(I)tetrafluoroborate;(-)-1,2-Bis((2R,5R)-2,5-dimethylphospholano)benzene(cyclooctadiene)rhodium (I) tetrafluoroborate;(-)-1,2-Bis((2R,5R)-2,5-dimethylphospholano)benzene(cyclooctadiene)rhodium(I) tetrafluoroborate;

IUPAC Name

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

InChI Key

ZUMNNKGIZSDCBZ-DBMWKRJKSA-N;

Complexity

369

Covalently-Bonded Unit Count

Defined Atom Stereocenter Count

EC Number

446-280-1

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

The product, (-)-1,2-Bis((2R,5R)-2,5-dimethylphospholano)benzene(1,5-cyclooctadiene)rhodium(I) tetrafluoroborate, 98+% (R,R)-Me-DUPHOS-Rh, serves as a vital component in catalyzing various asymmetric chemical reactions owing to its high efficiency and enantioselectivity. With its red or red-brown crystalline powder form, this ligand proves to be exceptionally effective in the asymmetric hydrogenation of substituted acetamidoacrylates, enol acetates, and tetrasubstituted enamides, achieving superior enantiomeric excesses. Notably, it enables the formation of advanced catalysts for asymmetric reductive aminations and hydrogenations of enol phosphonates. Additionally, it supports novel enantioselective syntheses of β-amino alcohols and 1,2-diamines, while also facilitating the catalytic asymmetric [4+1] cycloaddition of vinylallenes with CO and Rh-catalyzed asymmetric enyne cycloisomerizations. Furthermore, this product catalyzes the enantioselective addition of dialkylzinc to N-Diphenylphosphinoylimines and is involved in palladium-catalyzed asymmetric phosphination, making it a versatile and privileged ligand in various asymmetric transformations.

February 17, 2025

Highly Efficient Catalyst for Asymmetric Reactions

(-)-1,2-Bis((2R,5R)-2,5-dimethylphospholano)benzene(1,5-cyclooctadiene)rhodium(I) tetrafluoroborate is fantastic. In my research, it efficiently catalyzed asymmetric hydrogenation and cycloisomerization, delivering high enantiomeric excesses effortlessly.