Valence tautomerism in titanium enolates: catalytic radical haloalkylation and application in the total synthesis of neodysidenin.
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.
Beaumont
Stéphane
S
Department of Chemistry and Biochemistry, University of California, Santa Barbara, California 93106-9510, USA.
Ilardi
Elizabeth A
EA
Monroe
Lucas R
LR
Zakarian
Armen
A
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*
D000838:Anions; D004151:Dipeptides; D013844:Thiazoles; C414392:neodysidenin; D014025:Titanium