CAS 157904-67-1 2,2-Bis[2-(4R,5S-diphenyl-1,3-oxazolinyl)]propane, 95%

Synonyms

(4R,4'R,5S,5'S)-2,2'-(1-Methylethylidene)bis[4,5-dihydro-4,5-diphenyloxazole;157904-67-1;2,2'-Dimethylmethylenebis(4,5-diphenyl-4,5-dihydrooxazole);(4S,4'S,5R,5'R)-2,2'-(1-Methylethylidene)bis[4,5-dihydro-4,5-diphenyloxazole;157825-96-2;

IUPAC Name

2-[2-(4,5-diphenyl-4,5-dihydro-1,3-oxazol-2-yl)propan-2-yl]-4,5-diphenyl-4,5-dihydro-1,3-oxazole;

Molecular Weight

486.615g/mol

Molecular Formula

C33H30N2O2;

Canonical SMILES

CC(C)(C1=NC(C(O1)C2=CC=CC=C2)C3=CC=CC=C3)C4=NC(C(O4)C5=CC=CC=C5)C6=CC=CC=C6;

InChI

InChI=1S/C33H30N2O2/c1-33(2,31-34-27(23-15-7-3-8-16-23)29(36-31)25-19-11-5-12-20-25)32-35-28(24-17-9-4-10-18-24)30(37-32)26-21-13-6-14-22-26/h3-22,27-30H,1-2H3;

InChI Key

ZWWGNCSTEMMQOQ-UHFFFAOYSA-N;

Complexity

744

Covalently-Bonded Unit Count

Exact Mass

486.231g/mol

H-Bond Acceptor

Heavy Atom Count

Monoisotopic Mass

486.231g/mol

Rotatable Bond Count

Topological Polar Surface Area

43.2A^2

Undefined Atom Stereocenter Count

Application

The purpose of 2,2-Bis[2-(4R,5S-diphenyl-1,3-oxazolinyl)]propane, 95%, is to serve as a chiral ligand in various selective catalysis processes. It is instrumental in the development of selective exo-catalysts for enantioselective 1,3-dipolar cycloaddition reactions. Additionally, this compound facilitates the asymmetric aminooxygenation of alkenes, where it functions in conjunction with tetramethylaminopyridyl radical (TEMPO) as an oxidant and copper(II) triflate as a catalyst. It is also valuable in the asymmetric aminofluorination of olefins, particularly when utilizing an iron catalyst. Recently, this chiral Box ligand has been effectively used to mediate asymmetric aminofluorination of olefins involving Xtalfuor-E and TREAT-HF, resulting in cyclic carbamates that are readily convertible into beta-fluoro amino acids.

March 5, 2025

Excellent for Enantioselective Catalysis

Used 2,2-Bis[2-(4R,5S-diphenyl-1,3-oxazolinyl)]propane in our lab for asymmetric 1,3-dipolar cycloaddition. Easy to incorporate as a ligand, delivering precise chiral outcomes in our reactions. Highly recommend for research applications!