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Direct Catalytic Asymmetric 1,6-Conjugate Addition of Amides to p-Quinone Methides
Zhongdong Sun1, Bo Sun1, Naoya Kumagai1
1Institute of Microbial Chemistry (BIKAKEN) , 3-14-23 Kamiosaki , Shinagawa-ku, Tokyo 141-0021 , Japan.
Abstract:
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.
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