In vitro chemical synthesis demonstrates catalytic alkylative desymmetrization of alkynylcyclohexa-2,5-dienones, suggesting an efficient pathway to complex polycyclic pyrroles.
A catalytic [3 + 2]-cycloaddition/Friedel-Crafts alkylative desymmetrization strategy has been developed for the stereoselective construction of linear and bridged polycyclic pyrroles from alkynylcyclohexa-2,5-dienones. This strategy was further explored for the synthesis of 3-arylpyrroles under Brønsted acid catalysis. Reaction is highly chemo-, regio-, and stereoselective and is compatible with wide range of functionalized cyclohexa-2,5-dienones/pyrroles (>51 examples, ≤98% yields). Gram-scale synthesis and synthetic utility of the products have also been demonstrated to showcase the robustness of present method.
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Patel et al. (2022) studied this question.
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