title: Valence tautomerism in titanium enolates: catalytic radical haloalkylation and application in the total synthesis of neodysidenin.
abstract: A direct ruthenium-catalyzed radical chloroalkylation of N-acyl oxazolidinones capitalizing on valence tautomerism of titanium enolates has been developed. The chloroalkylation method served as the centerpiece in the enantioselective total synthesis of trichloroleucine-derived marine natural product neodysidenin.
authors.affiliation: Department of Chemistry and Biochemistry, University of California, Santa Barbara, California 93106-9510, USA.
authors.forename: Stéphane
authors.initials: S
authors.lastname: Beaumont
authors.forename: Elizabeth A
authors.initials: EA
authors.lastname: Ilardi
authors.forename: Lucas R
authors.initials: LR
authors.lastname: Monroe
authors.forename: Armen
authors.initials: A
authors.lastname: Zakarian
mesh_terms: D000838:Anions / Q000138:chemical synthesis*; D002384:Catalysis; D004151:Dipeptides / Q000138:chemical synthesis*; D008958:Models, Molecular; D015394:Molecular Structure; D013237:Stereoisomerism; D013844:Thiazoles / Q000138:chemical synthesis*; D014025:Titanium / Q000737:chemistry*
chemical_list: D000838:Anions; D004151:Dipeptides; D013844:Thiazoles; C414392:neodysidenin; D014025:Titanium