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  • Michael addition/pericyclization/rearrangement--a multicomponent strategy for the synthesis of substituted resorcinols.

Michael addition/pericyclization/rearrangement--a multicomponent strategy for the synthesis of substituted resorcinols.

Organic & biomolecular chemistry (2012-06-27)
Yu Liu, Michael P Doyle
ABSTRACT

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.

MATERIALS
Product Number
Brand
Product Description

Sigma-Aldrich
Lanthanum(III) trifluoromethanesulfonate, 99.999% trace metals basis
Sigma-Aldrich
Trifluoromethanesulfonic acid, ReagentPlus®, ≥99%
Sigma-Aldrich
Lithium trifluoromethanesulfonate, 96%
Sigma-Aldrich
Trifluoromethanesulfonic acid, reagent grade, 98%
Sigma-Aldrich
Lithium trifluoromethanesulfonate, 99.995% trace metals basis
Sigma-Aldrich
Zinc trifluoromethanesulfonate, 98%
Sigma-Aldrich
Silver trifluoromethanesulfonate, purum, ≥98.0% (Ag)
Sigma-Aldrich
Silver trifluoromethanesulfonate, ≥99%
Sigma-Aldrich
N-Phenylmaleimide, 97%
Sigma-Aldrich
Silver trifluoromethanesulfonate, ≥99.95% trace metals basis
Sigma-Aldrich
Aluminum trifluoromethanesulfonate, 99.9% trace metals basis
Sigma-Aldrich
3-Buten-2-one, contains 0.3-1.0% hydroquinone as stabilizer, technical grade, 90%