title: Oxazolines as Dual-Function Traceless Chromophores and Chiral Auxiliaries: Enantioselective Photoassisted Synthesis of Polyheterocyclic Ketones.
abstract: 2-(o-Amidophenyl)oxa- and -thiazolines undergo excited-state intramolecular proton transfer (ESIPT), generating aza-o-xylylenes capable of intramolecular [4+2] and [4+4] cycloadditions with tethered unsaturated pendants. Facile hydrolysis of the primary photoproducts, spiro-oxazolidines and thiazolidines, under mild conditions unmasks a phenone functionality. Variations in linkers allow for access to diverse core scaffolds in the primary photoproducts, rendering the approach compatible with the philosophy of diversity-oriented synthesis. Chiral oxazolines, readily available from the corresponding amino alcohols, yield enantioenriched keto-polyheterocycles of complex topologies with enantiomeric excess values up to 90%.
authors: Department of Chemistry and Biochemistry, University of Denver , Denver, Colorado 80208-2436, United States.
authors: Olga A
authors: OA
authors: Mukhina
authors: Department of Chemistry and Biochemistry, University of Denver , Denver, Colorado 80208-2436, United States.
authors: Andrei G
authors: AG
authors: Kutateladze
mesh_terms: D006571:Heterocyclic Compounds / Q000138:chemical synthesis* / Q000737:chemistry; D007659:Ketones / Q000138:chemical synthesis* / Q000737:chemistry; D015394:Molecular Structure; D010080:Oxazoles / Q000737:chemistry*; D055668:Photochemical Processes; D011108:Polymers / Q000138:chemical synthesis* / Q000737:chemistry; D013237:Stereoisomerism
chemical_list: D006571:Heterocyclic Compounds; D007659:Ketones; D010080:Oxazoles; D011108:Polymers