Synthesis of Polysubstituted 2-Piperidinones via a Michael Addition/Nitro-Mannich/Lactamization Cascade

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• 作者：Hui Liu ; Zhengquan Zhou ; Qian Sun ; Yun Li ; Yan Li ; Jinliang Liu ; Peiyun Yan ; Dandan Wang ; Cunde Wang
• 刊名：ACS Combinatorial Science
• 出版年：2012
• 出版时间：June 11, 2012
• 年：2012
• 卷：14
• 期：6
• 页码：366-371
• 全文大小：325K
• 年卷期：v.14,no.6(June 11, 2012)
• ISSN：2156-8944

文摘

An efficient and practical method has been developed for the diversity-oriented synthesis of polysubstituted 2-piperidinones via four-component reaction between substituted nitrostyrenes, aromatic aldehydes, ammonium acetate, and dialkyl malonates for the generation of a wide range of structurally interesting and pharmacologically significant compounds. It is worth mentioning that in the course of this reaction, the formation of products was highly stereoselective. Two differently stereochemical classes of polysubstituted 2-piperidinones depended on the substitutent position of aromatic aldehyde.

Keywords:

multicomponent reaction; polysubstituted piperidines; substituted nitrostyrenes; stereoselectivity; dialkyl malonates