Primary activation of para-quinone methides by chiral phosphoric acid for enantioselective construction of tetraarylmethanes.

Abstract

Demonstrated here is an asymmetric nucleophilic addition via primary activation of para-quinone methides (p-QMs) based on a chiral phosphoric acid catalytic system. In sharp contrast to previous CPA-based bifunctional activation processes that all required the nucleophiles to have an effective hydrogen bond donor unit (e.g., OH, NH), here no such unit is required in the nucleophile. N-protected indole nucleophiles were successfully utilized for the synthesis of chiral tetraarylmethanes with high efficiency and enantioselectivity under mild conditions. Therefore, this protocol significantly expanded the scope of asymmetric transformations of p-QMs.