Diastereoselective Synthesis of Rauhut–Currier-Type Adducts via an Unexpected α-Addition of α,β-Unsaturated γ-Butyrolactams to Coumarin Derivatives

详细信息    查看全文

• 作者：Shu-Mei Yang ; Ganapuram Madhusudhan Reddy ; Meng-Hsien Liu ; Tzu-Ping Wang ; Jhen-Kuei Yu ; Wenwei Lin
• 刊名：Journal of Organic Chemistry
• 出版年：2017
• 出版时间：January 6, 2017
• 年：2017
• 卷：82
• 期：1
• 页码：781-789
• 全文大小：456K
• ISSN：1520-6904

文摘

A novel, base-catalyzed and highly diastereoselective direct Michael addition-isomerization sequence is presented for the efficient synthesis of Rauhut–Currier-type adducts. An unexpected α-addition of γ-butyrolactam onto the 3-acyl coumarin derivatives was observed rather than the γ-addition, which is more common. The adducts could further undergo hydrolysis/decarboxylation to generate the products which are equivalent to those obtained by α-addition of γ-butyrolactam onto the corresponding chalcones.