Direct Catalytic Asymmetric 1,6-Conjugate Addition of Amides to p‑Quinone Methides

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 enantiomerical...

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Bibliographic Details
Published in:Organic letters 2018-05, Vol.20 (10), p.3070-3073
Main Authors: Sun, Zhongdong, Sun, Bo, Kumagai, Naoya, Shibasaki, Masakatsu
Format: Article
Language:English
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Summary: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.
ISSN:1523-7060
1523-7052
DOI:10.1021/acs.orglett.8b01109