title: DAST-mediated cyclization of α,α-disubstituted-α-acylaminoketones: efficient and divergent synthesis of unprecedented heterocycles.
abstract: The design of a new potent nonsteroidal ecdysone agonist led to the discovery of a diethylaminosulfur trifluoride (DAST)-mediated cyclization of α,α-disubstituted-α-acylaminoketones. The resulting fluorooxazolines can be ring-opened or selectively substituted by a range of nucleophiles to provide in high yields a diverse array of unprecedented heterocyclic frameworks.
authors.affiliation: Syngenta Crop Protection Münchwilen AG, Schaffhauserestrasse, CH-4332 Stein, Switzerland.
authors.forename: Aurélien
authors.initials: A
authors.lastname: Bigot
authors.forename: Judith
authors.initials: J
authors.lastname: Blythe
authors.forename: Chirag
authors.initials: C
authors.lastname: Pandya
authors.forename: Trixie
authors.initials: T
authors.lastname: Wagner
authors.forename: Olivier
authors.initials: O
authors.lastname: Loiseleur
mesh_terms: D002384:Catalysis; D020650:Combinatorial Chemistry Techniques; D003500:Cyclization; D004048:Diethylamines / Q000737:chemistry*; D005461:Fluorine / Q000737:chemistry*; D006573:Heterocyclic Compounds, 1-Ring / Q000138:chemical synthesis* / Q000737:chemistry; D007659:Ketones / Q000737:chemistry*; D015394:Molecular Structure; D010080:Oxazoles / Q000138:chemical synthesis* / Q000737:chemistry; D013237:Stereoisomerism
chemical_list: D004048:Diethylamines; D006573:Heterocyclic Compounds, 1-Ring; D007659:Ketones; D010080:Oxazoles; D005461:Fluorine; C040394:diethylaminosulfur trifluoride