Chiral Salicyloxazolines as Auxiliaries for the Asymmetric Synthesis of Ruthenium Polypyridyl Complexes was written by Gong, Lei; Mulcahy, Seann P.; Devarajan, Deepa; Harms, Klaus; Frenking, Gernot; Meggers, Eric. And the article was included in Inorganic Chemistry on September 6,2010.SDS of cas: 135948-04-8 The following contents are mentioned in the article:
Chiral auxiliaries are promising emerging tools for the asym. synthesis of octahedral metal complexes. The authors recently introduced chiral salicyloxazolines as coordinating bidentate chiral ligands which provide excellent control over the metal-centered configuration in ligand substitution reactions and can be removed afterward in an acid-induced fashion under complete retention of configuration. Here reported is the authors’ detailed study of this sequence of reactions, affording virtually enantiopure Ru polypyridyl complexes. The control of the metal-centered chirality by the coordinated chiral salicyloxazolinate ligand was evaluated as a function of reaction conditions, the employed bidentate 2,2′-bipyridine and 1,10-phenanthroline ligands, and the substituent at the asym. 5-position of the oxazoline heterocycle. Most striking was the strong influence of the reaction solvent, with aprotic solvents of lower polarity providing the most favorable diastereoselectivities. Through a combination of computational and exptl. results, the observed stereoselectivities are under thermodn. control. The removal of the chiral salicyloxazoline auxiliary under retention of the configuration requires acidic conditions and a coordinating solvent such as MeCN or THF to prevent partial racemization. This method represents the 1st general strategy for the asym. synthesis of enantiopure heteroleptic Ru polypyridyl complexes. This study involved multiple reactions and reactants, such as (S)-2-(4-(tert-Butyl)-4,5-dihydrooxazol-2-yl)phenol (cas: 135948-04-8SDS of cas: 135948-04-8).
(S)-2-(4-(tert-Butyl)-4,5-dihydrooxazol-2-yl)phenol (cas: 135948-04-8) belongs to oxazolidine derivatives. Oxazolidine-based compounds are well-known chiral auxiliaries and strategic molecular moieties in chemistry since they can effectively mask or mimic amino acid units or amino alcohols. In another report, the incorporation of an additional substituted oxazolidine ring over a range of new biphenylazepinium salt organocatalysts for the asymmetric epoxidation of alkenes improved enantiocontrol over the parent structures.SDS of cas: 135948-04-8
135948-04-8;(S)-2-(4-(tert-Butyl)-4,5-dihydrooxazol-2-yl)phenol;The future of 135948-04-8;New trend of C13H17NO2;function of 135948-04-8