Direct Catalytic Asymmetric Mannich-Type Reaction of Alkylamides

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• 作者：Fernando Arteaga Arteaga ; Zijian Liu ; Lennart Brewitz ; Jianyang Chen ; Bo Sun ; Naoya Kumagai ; Masakatsu Shibasaki
• 刊名：Organic Letters
• 出版年：2016
• 出版时间：May 20, 2016
• 年：2016
• 卷：18
• 期：10
• 页码：2391-2394
• 全文大小：376K
• 年卷期：0
• ISSN：1523-7052

文摘

Direct enolate formation coupled with subsequent enantioselective C–C bond formation remains a topic of intense interest in asymmetric catalysis. This methodology is achieved even with low acidic amides without an electron-withdrawing group at the α-position in the context of a Mannich-type reaction. Acetate-, propionate-, and butyrate-type 7-azaindoline amides served as enolate precursors to afford the desired Mannich adducts with high stereoselectivity, and ligand-enabled diastereo-divergency provided access to both anti/syn diastereomers. The facile transformation of the amide moiety ensures the synthetic utility of the Mannich adducts.