Organocatalytic Remote Stereocontrolled Synthesis of Tetrasubstituted Allenes via Asymmetric 1,8‐Addition of Propargylic Aza‐p‐Quinone Methides

Abstract

AbstractAn organocatalytic remote stereocontrolled 1,8‐conjugated addition of in situ formed propargylic aza‐p‐QMs from α‐(4‐aminophenyl) propargylic alcohols and indole‐2‐carboxylates was developed, affording axially chiral tetrasubstituted allenes in 62–99% yield with 52–99% ee. The synthetic strategy not only enriches the chemistry of aza‐p‐quinone methides, but also provides an alternative tool for the preparation of axially chiral tetrasubstituted allenes.