Organocatalytic Stereoselective 1,10‐Conjugate Addition of Indole‐2‐Carboxylates to Alkynyl Aza‐2,4′‐Biphenyl Quinone Methides

Remote stereocontrolled functionalization plays a pivotal role in organic synthesis, particularly in the construction of chiral molecular frameworks. In this context, the organocatalytic remote conjugate addition to in situ generated conjugate systems derived from α‐functionalized alcohols offers a robust synthetic strategy. Herein, we report a chiral phosphoric acid‐catalyzed 1,10‐conjugate addition of indole‐2‐carboxylates to aza‐2,4′‐biphenyl quinone methides (aza‐2,4′‐BQMs), which are readily generated in situ from α‐[4‐(2‐aminophenyl)phenyl]propargyl alcohols. This transformation enables the efficient construction of axially chiral tetrasubstituted allenes in good yields and enantioselectivities. Importantly, this study not only broadens the scope of highly reactive aza‐biphenyl quinone methides but also enriches the synthetic toolbox for enantioselective transformations involving aza‐QMs.