Direct Catalytic Asymmetric Aldol Reaction of α-Alkylamides

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• 作者：Zijian Liu ; Toshifumi Takeuchi ; Roman Pluta ; Fernando Arteaga Arteaga ; Naoya KumagaiMasakatsu Shibasaki
• 刊名：Organic Letters
• 出版年：2017
• 出版时间：February 3, 2017
• 年：2017
• 卷：19
• 期：3
• 页码：710-713
• 全文大小：364K
• ISSN：1523-7052

文摘

A catalytic asymmetric aldol reaction directly employing amides as latent enolates has remained elusive because of the resistance of amides to enolization. A direct aldol reaction of α-alkylamides without any electron-withdrawing group harnessed by specific activation of 7-azaindoline amides under soft Lewis acid/Brønsted base cooperative catalysis is reported. Diastereo- and enantioselective coupling with ynals and aromatic aldehydes as well as divergent functional group interconversion of the amide provided expeditious access to a variety of aliphatic and aromatic chiral building blocks.