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

Shu Mei Yang, Ganapuram Madhusudhan Reddy, Meng Hsien Liu, Tzu Ping Wang, Jhen Kuei Yu, Wenwei Lin*

*此作品的通信作者

研究成果: 雜誌貢獻期刊論文同行評審

15 引文 斯高帕斯(Scopus)

摘要

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.

原文英語
頁(從 - 到)781-789
頁數9
期刊Journal of Organic Chemistry
82
發行號1
DOIs
出版狀態已發佈 - 2017 一月 6

ASJC Scopus subject areas

  • 有機化學

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