Direct Catalytic Asymmetric 1,6-Conjugate Addition of Amides to p-Quinone Methides.
Zhongdong SunBo SunNaoya KumagaiMasakatsu ShibasakiPublished in: Organic letters (2018)
Amide pronucleophiles were successfully incorporated into a 1,6-conjugate addition reaction manifold using p-quinone methides ( p-QMs) as electrophiles. Four different types of functionalities were tolerated as α-substituents of the amides, allowing for expeditious access to a range of enantiomerically enriched diarylmethine products. The 7-azaindoline unit is critically important for in situ catalytic enolization of the amide pronucleophile, engaging in 1,6-conjugate addition to p-QMs with readily available catalyst components.