Abstract
An organocatalytic enantioselective reaction utilizing α‐[4‐(4‐hydroxyphenyl)phenyl]propargyl alcohols and 3‐substituted indoles has been successfully established for the synthesis of chiral 3H‐pyrrolo[1,2‐a]indoles. Through the assistance of an appropriate chiral phosphoric acid, a cascade sequence is facilitated, beginning with the dehydration of α‐[4‐(4‐hydroxyphenyl)phenyl]propargyl alcohols to form alkynyl 4,4′‐biphenyl quinone methides (4,4′‐BQMs). Subsequently, 1,12‐addition of 3H‐pyrrolo[1,2‐a]indoles to these alkynyl 4,4′‐BQMs results in the formation of allenes, which are then protonated and regenerate 4,4′‐BQMs. Finally, an enantioselective intramolecular annulation of 4,4′‐BQMs occurs smoothly, leading to the production of a range of 3H‐pyrrolo[1,2‐a]indoles with high efficiency and asymmetric induction.
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