CAS 443347-10-2 (S)-Xyl-PPhos - Catalysts / Alfa Chemistry

Synonyms

(S)-(-)-2,2',6,6'-Tetramethoxy-4,4'-bis[di(3,5-xylyl)phosphino]-3,3'-bipyridine

Molecular Weight

756.85

Molecular Formula

C46H50N2O4P2

Canonical SMILES

COc1cc(P(c2cc(C)cc(C)c2)c3cc(C)cc(C)c3)c(c(OC)n1)-c4c(OC)nc(OC)cc4P(c5cc(C)cc(C)c5)c6cc(C)cc(C)c6

InChI

1S/C46H50N2O4P2/c1-27-13-28(2)18-35(17-27)53(36-19-29(3)14-30(4)20-36)39-25-41(49-9)47-45(51-11)43(39)44-40(26-42(50-10)48-46(44)52-12)54(37-21-31(5)15-32(6)22-37)38-23-33(7)16-34(8)24-38/h13-26H,1-12H3

InChI Key

JRTHAKOHBMETRC-UHFFFAOYSA-N

Melting Point

158-162 °C

Assay

0.97

Application

The purpose of (S)-Xyl-PPhos is to serve as a versatile chiral ligand that plays a crucial role in various pharmaceutical and industrial applications. It is effectively utilized in the asymmetric hydrogenation of β-keto esters, 2-arylacrylates, aryl ketones, and other substrates, ensuring precision in enantioselective transformations. As a chiral ligand, it facilitates enantioselective rhodium-catalyzed [2+2+2] carbocyclization reactions and supports ruthenium-catalyzed hydrogenation of (E)-β-(acylamino)acrylates to yield β-amino acids. When paired with rhodium, it achieves superior enantioselectivity in the hydrogenation of (Z)-β-(acylamino)acrylates. Additionally, (S)-Xyl-PPhos is employed in copper-catalyzed asymmetric hydrosilylation of ketones and serves as a critical component in asymmetric allylic substitution reactions with boronic acids as nucleophiles. Its utility extends to providing beneficial selectivity in asymmetric Pauson-Khand-type cyclizations, making it an indispensable tool in the advancement of precise chemical syntheses.

February 10, 2025

Exceptional Chiral Ligand for Asymmetric Reactions

I used (S)-Xyl-PPhos in asymmetric hydrogenation and obtained excellent enantioselectivity. It's ideal for pharmaceutical applications and produced consistent results in enantioselective rhodium-catalyzed reactions, enhancing research productivity significantly.