Search results for "Para-quinone"
showing 3 items of 3 documents
Asymmetric Synthesis of Spiro-oxindole-ε-lactones through N-Heterocyclic Carbene Catalysis
2018
An unprecedented N-heterocyclic carbene-catalyzed annulation of isatin-derived enals and o-hydroxyphenyl-substituted p-quinone methides as bifunctional reagents has been discovered. The new protocol involves a 1,6-addition of the homoenolate equivalent intermediates to the hydroxy donor-1,6-Michael acceptors and leads to spirocyclic oxindole-ε-lactones in high yields and very good stereoselectivities.
Organocatalytic Domino Oxa-Michael/1,6-Addition Reactions: Asymmetric Synthesis of Chromans Bearing Oxindole Scaffolds.
2016
An asymmetric organocatalytic domino oxa-Michael/1,6-addition reaction of ortho-hydroxyphenyl-substituted para-quinone methides and isatin-derived enoates has been developed. In the presence of 5 mol % of a bifunctional thiourea organocatalyst, this scalable domino reaction affords 4-phenyl-substituted chromans bearing spiro-connected oxindole scaffolds and three adjacent stereogenic centers in good to excellent yields (up to 98 %) and with very high stereoselectivities (up to >20:1 d.r., >99 % ee).
Synthesis of trans-disubstituted-2,3-dihydrobenzofurans by a formal [4 + 1] annulation between para-quinone methides and sulfonium salts
2018
An efficient protocol for the synthesis of trans-disubstituted-2,3-dihydrobenzofurans through [4 + 1] annulation of para-quinone methides with sulfonium salts has been developed. Under very mild conditions this unprecedented reaction occurs in good to excellent yields (up to 99%), offering a straightforward access to a variety of 2,3-dihydrobenzofurans.