CAS 213343-64-7 (+)-1,2-Bis((2S,5S)-2,5-diethylphospholano)benzene(1,5-cyclooctadiene)rhodium(I) tetrafluoroborate, 98+% (S,S)-Et-DUPHOS-Rh

Synonyms

(S,S)-Et-DUPHOS-Rh;213343-64-7;1,2-Bis((2S,5S)-2,5-diethylphospholano)benzene(cyclooctadiene)rhodium(I) tetrafluoroborate, 97%;DTXSID60451539;XIOPHSBHVOCZMM-ZCTOJWETSA-N;J-014000;1,2-Bis[(2S,5S)-2,5-diethylphospholano]benzene(1,5-cyclooctadiene)rhodium(I) tetrafluoroborate;

IUPAC Name

(1Z,5Z)-cycloocta-1,5-diene;(2S,5S)-1-[2-[(2S,5S)-2,5-diethylphospholan-1-yl]phenyl]-2,5-diethylphospholane;rhodium;tetrafluoroborate;

Molecular Weight

660.371g/mol

Molecular Formula

C30H48BF4P2Rh-;

Canonical SMILES

[B-](F)(F)(F)F.CCC1CCC(P1C2=CC=CC=C2P3C(CCC3CC)CC)CC.C1CC=CCCC=C1.[Rh];

InChI

InChI=1S/C22H36P2.C8H12.BF4.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)5;/h9-12,17-20H,5-8,13-16H2,1-4H3;1-2,7-8H,3-6H2;;/q;;-1;/b;2-1-,8-7-;;/t17-,18-,19-,20-;;;/m0.../s1;

InChI Key

XIOPHSBHVOCZMM-ZCTOJWETSA-N;

Complexity

414

Covalently-Bonded Unit Count

Defined Atom Stereocenter Count

Defined Bond Stereocenter Count

Exact Mass

660.232g/mol

Formal Charge

-1

H-Bond Acceptor

Heavy Atom Count

Monoisotopic Mass

660.232g/mol

Rotatable Bond Count

Topological Polar Surface Area

0A^2

Application

(+)-1,2-Bis((2S,5S)-2,5-diethylphospholano)benzene(1,5-cyclooctadiene)rhodium(I) tetrafluoroborate, 98+% (S,S)-Et-DUPHOS-Rh serves as a highly efficient catalyst in various asymmetric synthesis processes. It plays a crucial role in the preparation of the B precursor of cryptophycins through the Horner-Wadsworth-Emmons reaction and asymmetric hydrogenation. Additionally, it is instrumental in synthesizing constrained phenylalanine analogs via the Heck reaction, followed by asymmetric hydrogenation and cyclization. This catalyst supports the enantioselective production of N-benzyloxy-β-amino acid methyl esters and the formation of fluoro amino acids, which are key components in developing potent macrocyclic HCV NS3 protease inhibitors. It is also utilized in the stereoselective preparation of triply isotope-labeled Ser, Cys, and Ala, as well as β-amino acids from asymmetric hydrogenation of α-(aminomethyl)acrylates. Furthermore, it is applied in asymmetric hydrogenation of primary and secondary amino ketones, facilitating the asymmetric synthesis of compounds like (-)-arbutamine and (-)-denopamine. This ligand also shows efficacy in the Rh-catalyzed asymmetric hydrogenation of α-aminomethylacrylates and 2-methylenesuccinamic acid.

January 28, 2025

Efficient Catalyst for Asymmetric Synthesis

I used (S,S)-Et-DUPHOS-Rh from Alfa Chemistry for asymmetric hydrogenation in synthesizing precursor B of cryptophycin. It performed excellently, enhancing enantioselectivity in our constrained phenylalanine analog projects. Highly recommend for precision-critical research.