Pericyclic reaction of a zwitterionic salt of an enedione-diazoester. A novel strategy for the synthesis of highly functionalized resorcinols.
Enedione-diazoesters formed from 3-TBSO-2-diazo-3-butenoates undergo base-catalyzed pericyclization that with dinitrogen extrusion and methyl migration provide a novel and efficient route to 2-carboalkoxyresorcinols. Intercepting the intermediate enolate anion with methyl vinyl ketone leads to the corresponding 4-substituted 2-carboalkoxyresorcinol and suggests generalization of this methodology.
Liu
Yu
Y
Department of Chemistry and Biochemistry, University of Maryland, College Park, Maryland 20742, USA.
Bakshi
Kanwarpal
K
Zavalij
Peter
P
Doyle
Michael P
MP
D001391:Azo Compounds / Q000737:chemistry*; D002384:Catalysis; D018360:Crystallography, X-Ray; D003500:Cyclization; D008958:Models, Molecular; D015394:Molecular Structure; D012118:Resorcinols / Q000138:chemical synthesis*; D012492:Salts / Q000737:chemistry*
D001391:Azo Compounds; D012118:Resorcinols; D012492:Salts; C006666:azoester
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