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A new catalytic reaction to synthesize structurally complex hexahydrochromeno[2,3-b]pyrrole derivatives from simple 3butynamine and 2-(hydroxymethyl)phenol derivatives is described. The process is promoted by a dual catalytic system formed by a… Click to show full abstract
A new catalytic reaction to synthesize structurally complex hexahydrochromeno[2,3-b]pyrrole derivatives from simple 3butynamine and 2-(hydroxymethyl)phenol derivatives is described. The process is promoted by a dual catalytic system formed by a gold complex and a Lewis acid (boron trifluoride). The reaction involves the synchronized transformation of the starting materials into two reactive intermediates, a cyclic enamine derivative and an orthoquinone methide, that subsequently react between them through a formal [4+2] cycloaddition to furnish the final poly-heterocyclic product in a straightforward way.
Journal Title: European Journal of Organic Chemistry
Year Published: 2018
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