2‐(4,5‐Dihydro‐4‐Phenyl‐2‐Oxazolyl)Phenol

( S )‐enantiomer image [135948‐05‐9] C 15 H 13 NO 2 (MW 239.27) InChI = 1S/C15H13NO2/c17‐14‐9‐5‐4‐8‐12(14)15‐16‐13(10‐18‐15)11‐6‐2‐1‐3‐7‐11/h1‐9,13,17H,10H2/t13‐/m1/s1 InChIKey = IZKPOGDNFMTRFD‐CYBMUJFWSA‐N SMILES: C1[C@@H](N=C(O1)C2=CC=CC=C2O)C3=CC=CC=C3 Canonical SMILES: OC1=C(C=CC=C1)C1=N[C@H](CO1)C1=CC=CC=C1 ( R )‐enantiomer image [150699‐08‐4] C 15 H 13 NO 2 (MW 239.27) InChI = 1S/C15H13NO2/c17‐14‐9‐5‐4‐8‐12(14)15‐16‐13(10‐18‐15)11‐6‐2‐1‐3‐7‐11/h1‐9,13,17H,10H2/t13‐/m0/s1 InChIKey = IZKPOGDNFMTRFD‐ZDUSSCGKSA‐N SMILES: C1[C@H](N=C(O1)C2=CC=CC=C2O)C3=CC=CC=C3 Canonical SMILES: OC1=CC=CC=C1C1=N[C@@H](CO1)C1=CC=CC=C1 racemate image [760952‐77‐0] C 15 H 13 NO 2 (MW 239.27) InChI = 1S/C15H13NO2/c17‐14‐9‐5‐4‐8‐12(14)15‐16‐13(10‐18‐15)11‐6‐2‐1‐3‐7‐11/h1‐9,13,17H,10H2 InChIKey = IZKPOGDNFMTRFD‐UHFFFAOYSA‐N SMILES: C1C(N=C(O1)C2=CC=CC=C2O)C3=CC=CC=C3 Canonical SMILES: [H][C@@]1(COC(=N1)C1=C(O)C=CC=C1)C1=CC=CC=C1 (chiral ligand for the synthesis of N,O‐ligated metal complexes, 1–5 asymmetric allylic substitution reactions, 6 asymmetric functionalization of alkenes, 7–9 and enantioselective CH activation 10–15 ). Alternative Name(s) : 2‐(4‐phenyl‐4,5‐dihydrooxazol‐2‐yl)phenol, salicyloxazoline (Salox); phenol‐oxazoline. Physical Data : bp 185 °C/0.02 mbar, = +40.4 ( c 2.27, toluene) for ( S )‐ 1 ; 1 mp 36–37 °C, = +122.4° ( c 1.0, CHCl 3 ) for ( R )‐ 1 . 16 Solubility : soluble in most organic solvents such as dichloromethane, toluene, methanol, and ethyl acetate. Form Supplied in : white solid; commercially available. Analysis of Reagent Purity : 1 H NMR (400 MHz, CDCl 3 ) δ 12.14 (s, 1 H ), 7.72 (dd, J = 7.6, 1.6 Hz, 1 H ), 7.43–7.28 (m, 6 H ), 7.04 (dd, J = 8.4, 0.8 Hz, 1 H ), 6.90 (td, J = 7.6, 1.2 Hz, 1 H ), 5.46 (dd, J = 10.0, 8.4 Hz, 1 H ), 4.79 (dd, J = 10.0, 8.4 Hz, 1 H ), 4.24 (t, J = 8.0 Hz, 1 H