387401-16-3Relevant academic research and scientific papers
Convergent synthesis of 2H-chromenes - A formal [3+3] cycloaddition by a one-pot, three-step cascade
Parker, Kathlyn A.,Mindt, Thomas L.
, p. 9779 - 9786 (2012/02/05)
In cases in which the palladium-catalyzed coupling of a bromoquinone with a vinyl stannane affords a vinyl quinone that enolizes, the resulting ortho-quinone methide undergoes an oxa-6π electrocyclization. Enolization is promoted by the presence of a pola
Electrocyclic ring closure of the enols of vinyl quinones. A 2H-chromene synthesis
Parker, Kathlyn A.,Mindt, Thomas L.
, p. 3875 - 3878 (2007/10/03)
equation presented Thermolysis of enolizable vinyl quinones in polar, aprotic media provides 2H-chromenes. Experimental evidence supports a two-step mechanism in which enolization is followed by a thermal 6π-electrocyclic reaction of an intermediate quinone methide. Application of this method led to the total synthesis of the reputed structure of an Ageratum juvenile hormone. When enolizable vinyl quinones are the products of Stille coupling, the chromene annulation product is obtained directly.
