CAS 569650-64-2 (+)-1,2-Bis((2R,5R)-2,5-di-i-propylphospholano)benzene)1,5-cyclooctadiene)rhodium(I) tetrafluoroborate, min. 98% (R,R)-i-Pr-DUPHOS-Rh

Synonyms

569650-64-2;1,2-Bis[(2R,5R)-2,5-diisopropylphospholano]benzene(1,5-cyclooctadiene)rhodium(I) tetrafluoroborate;(R,R)-i-Pr-DUPHOS-Rh;DTXSID00514132;PUBCHEM_12964416;MFCD07369039;(+)-1,2-Bis((2R,5R)-2,5-di-i-propylphospholano)benzene(1,5-cyclooctadiene)rhodium(I) tetrafluoroborate;(+)-1,2-Bis((2R,5R)-2,5-di-i-propylphospholano)benzene)1,5-cyclooctadiene)rhodium(i)tetrafluoroborate;

IUPAC Name

(1Z,5Z)-cycloocta-1,5-diene;(2R,5R)-1-[2-[(2R,5R)-2,5-di(propan-2-yl)phospholan-1-yl]phenyl]-2,5-di(propan-2-yl)phospholane;rhodium;tetrafluoroborate;

Molecular Weight

716.479g/mol

Molecular Formula

C34H56BF4P2Rh-;

Canonical SMILES

[B-](F)(F)(F)F.CC(C)C1CCC(P1C2=CC=CC=C2P3C(CCC3C(C)C)C(C)C)C(C)C.C1CC=CCCC=C1.[Rh];

InChI

InChI=1S/C26H44P2.C8H12.BF4.Rh/c1-17(2)21-13-14-22(18(3)4)27(21)25-11-9-10-12-26(25)28-23(19(5)6)15-16-24(28)20(7)8;1-2-4-6-8-7-5-3-1;2-1(3,4)5;/h9-12,17-24H,13-16H2,1-8H3;1-2,7-8H,3-6H2;;/q;;-1;/b;2-1-,8-7-;;/t21-,22-,23-,24-;;;/m1.../s1;

InChI Key

IJKOQQHIAGRJHA-QPZXYOTCSA-N;

Complexity

499

Covalently-Bonded Unit Count

Defined Atom Stereocenter Count

Defined Bond Stereocenter Count

Exact Mass

716.294g/mol

Formal Charge

-1

H-Bond Acceptor

Heavy Atom Count

Monoisotopic Mass

716.294g/mol

Rotatable Bond Count

Topological Polar Surface Area

0A^2

Application

The purpose of (+)-1,2-Bis((2R,5R)-2,5-di-i-propylphospholano)benzene)1,5-cyclooctadiene)rhodium(I) tetrafluoroborate, also known as (R,R)-i-Pr-DUPHOS-Rh, is to serve as an exceptionally efficient catalyst within the DUPHOS family for a variety of asymmetric transformations. This compound is particularly effective in the hydrogenation of diverse substituted acetamidoacrylates and enol acetates, achieving high enantiomeric excesses. It is utilized to facilitate the hydrogenation of tetrasubstituted enamides and forms superior catalysts for asymmetric reductive aminations and hydrogenation of enol phosphonates. Additionally, it supports enantioselective syntheses, such as the production of β-amino alcohols and 1,2-diamines. It acts as a critical ligand in catalytic asymmetric processes, including the [4+1] cycloaddition of vinylallenes with CO, Rh-catalyzed enyne cycloisomerization, and the enantioselective addition of dialkylzinc to N-Diphenylphosphinoylimines. Furthermore, it plays a role in palladium-catalyzed asymmetric phosphination, enhancing the efficiency and selectivity of these advanced chemical processes.

February 18, 2025

Highly Efficient Catalyst for Asymmetric Synthesis

I used Alfa Chemistry's (R,R)-i-Pr-DUPHOS-Rh in my research for asymmetric hydrogenation. It efficiently catalyzed enol phosphonates, delivering high enantiomeric excess. This catalyst greatly advanced my synthesis of β-amino alcohols. Highly recommend for enyne cycloisomerization too!