Multifunctionalized 3-hydroxypyrroles in a three-step, one-pot cascade process from methyl 3-TBSO-2-diazo-3-butenoate and nitrones.
The synthesis of N-aryl-2-carboxyl-3-hydroxy-5-arylpyrroles has been achieved in high yield by the combination of a TBSO-substituted vinyldiazoacetate and nitrones in a one-pot cascade process involving copper-catalyzed Mannich addition, dirhodium-catalyzed dinitrogen extrusion and N-OTBS insertion, and acid-promoted aromatization (elimination).
Department of Chemistry and Biochemistry, University of Maryland, College Park, Maryland 20742, United States.
Xinfang
X
Xu
Maxim O
MO
Ratnikov
Peter Y
PY
Zavalij
Michael P
MP
Doyle
D020148:Butyric Acid / Q000737:chemistry*; D002384:Catalysis; D003300:Copper / Q000737:chemistry; D006900:Hydroxylation; D008958:Models, Molecular; D015394:Molecular Structure; D009589:Nitrogen Oxides / Q000737:chemistry*; D011758:Pyrroles / Q000138:chemical synthesis*
D009589:Nitrogen Oxides; D011758:Pyrroles; C015388:nitrones; D020148:Butyric Acid; D003300:Copper