CAS 866081-62-1 (R,R)-(-)-2,3-Bis(t-butylmethylphosphino)quinoxaline, min. 98% (R,R)-QuinoxP*

Synonyms

AK173366; 866081-62-1; (R,R)-(-)-2,3-Bis(tert-butylmethylphosphino)quinoxaline; (R,R)-QuinoxP; (R,R)-(-)-2,3-Bis(t-butylmethylphosphino)quinoxaline;

IUPAC Name

(R)-tert-butyl-[3-[tert-butyl(methyl)phosphanyl]quinoxalin-2-yl]-methylphosphane;

Molecular Weight

334.384g/mol

Molecular Formula

C18H28N2P2;

Canonical SMILES

CC(C)(C)P(C)C1=NC2=CC=CC=C2N=C1P(C)C(C)(C)C;

InChI

InChI=1S/C18H28N2P2/c1-17(2,3)21(7)15-16(22(8)18(4,5)6)20-14-12-10-9-11-13(14)19-15/h9-12H,1-8H3/t21-,22-/m0/s1;

InChI Key

DRZBLHZZDMCPGX-VXKWHMMOSA-N;

Complexity

336

Covalently-Bonded Unit Count

Defined Atom Stereocenter Count

Exact Mass

334.173g/mol

H-Bond Acceptor

Heavy Atom Count

Monoisotopic Mass

334.173g/mol

Rotatable Bond Count

Topological Polar Surface Area

25.8A^2

Application

(R,R)-QuinoxP*, with a minimum purity of 98%, serves as a highly efficient and air-stable chiral ligand. It plays a crucial role in promoting enantioselective transformations across a variety of catalytic processes. The ligand is notably effective in rhodium-catalyzed asymmetric hydrogenations of dehydroamino acid esters and α-enamides, as well as 1,4-additions of arylboronic acids to α,β-unsaturated carbonyl compounds. Additionally, it facilitates rhodium-catalyzed asymmetric alkylative ring openings and hydroacylations, palladium-catalyzed asymmetric allylic alkylations and aminations, ruthenium-catalyzed asymmetric hydrogenations of ketones, and silver-catalyzed asymmetric nitroso aldol reactions. Further extending its versatility, (R,R)-QuinoxP* is instrumental in copper-catalyzed enantioconvergent allylic borylations and enantioselective cyclopropylations, consistently exhibiting high levels of enantiocontrol in these diverse synthetic transformations.

January 3, 2025

A Game-Changer for Enantioselective Catalysis

I utilized (R,R)-QuinoxP in asymmetric hydrogenations. Its air-stability and high enantiocontrol were pivotal. Perfect for complex transformations in synthetic chemistry research. Highly recommend for precision in catalytic processes.