Michael addition/pericyclization/rearrangement--a multicomponent strategy for the synthesis of substituted resorcinols.
The combination of methyl 3,7-dioxo-2-diazo-4-octenoate from the zinc triflate catalyzed Mukaiyama-Michael reaction of methyl 3-tert-butylsilyloxy-2-diazobutenoate and 4-methoxy-3-buten-2-one with Michael acceptors (methyl vinyl ketone, N-phenylmaleimide, β-nitrovinylarenes) in the presence of a catalytic amount of base provides convenient access to highly substituted resorcinol derivatives. This transformation is achieved in an efficient one-pot multi-component transformation by the sequential addition of the reagents.
Department of Chemistry and Biochemistry, University of Maryland, College Park, Maryland 20742, USA.
Yu
Y
Liu
Michael P
MP
Doyle
D002074:Butanones / Q000737:chemistry; D002384:Catalysis; D008301:Maleimides / Q000737:chemistry; D008698:Mesylates / Q000737:chemistry; D012118:Resorcinols / Q000138:chemical synthesis* / Q000737:chemistry
D002074:Butanones; D008301:Maleimides; D008698:Mesylates; D012118:Resorcinols; C028525:N-phenylmaleimide; C057920:3-buten-2-one; C012077:trifluoromethanesulfonic acid