Application In Synthesis of (R)-4-(tert-Butyl)-2-(5-(trifluoromethyl)pyridin-2-yl)-4,5-dihydrooxazole. The protonation of heteroatoms in aromatic heterocycles can be divided into two categories: lone pairs of electrons are in the aromatic ring conjugated system; and lone pairs of electrons do not participate. Compound: (R)-4-(tert-Butyl)-2-(5-(trifluoromethyl)pyridin-2-yl)-4,5-dihydrooxazole, is researched, Molecular C13H15F3N2O, CAS is 1428537-19-2, about Enantioselective construction of remote quaternary stereocentres. Author is Mei, Tian-Sheng; Patel, Harshkumar H.; Sigman, Matthew S..
Small mols. that contain all-carbon quaternary stereocenters-carbon atoms bonded to four distinct carbon substituents-are found in many secondary metabolites and some pharmaceutical agents. The construction of such compounds in an enantioselective fashion remains a long-standing challenge to synthetic organic chemists. In particular, methods for synthesizing quaternary stereocenters that are remote from other functional groups are underdeveloped. Here we report a catalytic and enantioselective intermol. Heck-type reaction of trisubstituted-alkenyl alcs. with aryl boronic acids. This method provides direct access to quaternary all-carbon-substituted β-, γ-, δ-, ε- or ζ-aryl carbonyl compounds, because the unsaturation of the alkene is relayed to the alc., resulting in the formation of a carbonyl group. The scope of the process also includes incorporation of pre-existing stereocenters along the alkyl chain, which links the alkene and the alc., in which the stereocenter is preserved. The method described allows access to diverse mol. building blocks containing an enantiomerically enriched quaternary center.
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