CAS 174500-20-0 (S,S)-2,6-Bis(4-phenyl-2-oxazolin-2-yl)pyridine

Synonyms

BP-12297; SC-44215; 2,6-BIS[(S)-4-PHENYL-2-OXAZOLIN-2-YL]PYRIDINE; RTR-007742; BR-10750; (S,S)-2,6-Bis(4-phenyl-2-oxazolinyl)pyridine; AB1011206; AJ-35446; ANW-22713; J-010994;

IUPAC Name

(4S)-4-phenyl-2-[6-[(4S)-4-phenyl-4,5-dihydro-1,3-oxazol-2-yl]pyridin-2-yl]-4,5-dihydro-1,3-oxazole;

Molecular Weight

369.424g/mol

Molecular Formula

C23H19N3O2;

Canonical SMILES

C1C(N=C(O1)C2=NC(=CC=C2)C3=NC(CO3)C4=CC=CC=C4)C5=CC=CC=C5;

InChI

InChI=1S/C23H19N3O2/c1-3-8-16(9-4-1)20-14-27-22(25-20)18-12-7-13-19(24-18)23-26-21(15-28-23)17-10-5-2-6-11-17/h1-13,20-21H,14-15H2/t20-,21-/m1/s1;

InChI Key

HLHBIMJNCKZZQO-NHCUHLMSSA-N;

Storage

Refrigerator

Complexity

543

Covalently-Bonded Unit Count

Defined Atom Stereocenter Count

Exact Mass

369.148g/mol

H-Bond Acceptor

Heavy Atom Count

Monoisotopic Mass

369.148g/mol

Rotatable Bond Count

Topological Polar Surface Area

56.1A^2

UNII

5R62CXU58K

Application

(S,S)-2,6-Bis(4-phenyl-2-oxazolin-2-yl)pyridine serves as a versatile ligand designed to facilitate a range of enantioselective and asymmetric catalytic reactions. It effectively partners with various metals such as copper, tin, ytterbium, scandium, europium, indium, and iron, enabling a diverse set of applications. These include the syn-selective Mukaiyama aldol reaction, anti-selective aldol reaction, and desymmetrization of meso epoxides. Additionally, it enhances the enantioselective addition of terminal alkynes to imines, asymmetric alkynylation of cyclic azomethine imines and oxocarbenium ions, and intramolecular propargylic amination. This ligand also supports reactions like symmetric hydroxylation, azide-alkyne cycloaddition to quaternary oxindoles, nitrene transfer to sulfides, enantioselective construction of spiro-fused 2-oxindole/α-methylene-γ-butyrolactones, and the dearomatization of 2-naphthols by electrophilic amination. Its broad application demonstrates its critical role in advancing catalytic processes across various chemical transformations.

January 18, 2025

Invaluable Ligand for Complex Reactions

(S,S)-2,6-Bis(4-phenyl-2-oxazolin-2-yl)pyridine worked impressively in my research, facilitating copper-catalyzed azide-alkyne cycloadditions efficiently. This white solid enhanced reaction selectivity, crucial for synthesizing complex compounds. Highly recommend for advanced chemical synthesis.