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

Research output: Contribution to journalArticlepeer-review

14 Citations (Scopus)

Abstract

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.

Original languageEnglish
Pages (from-to)781-789
Number of pages9
JournalJournal of Organic Chemistry
Volume82
Issue number1
DOIs
Publication statusPublished - 2017 Jan 6

ASJC Scopus subject areas

  • Organic Chemistry

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