Intermolecular [3+2] MIRC reactions with alkynoates. Asymmetric Michael addition leading to a nonracemic cyclopentene-annulated α,β-butenolide

Philippe Nakache, Eugene Ghera, Alfred Hassner

Research output: Contribution to journalArticlepeer-review

10 Scopus citations

Abstract

A novel Michael-initiated ring closure reacton involving allylic chlorosulfone (2) and γ-alkoxy-α,β-ynoates to afford 4- methylenecyclopentenecarboxylates is reported, while with γ-alkylynoates no reaction occurred. With chiral phenyl ynoates 4, the reaction proceeds by 1,3-asymmetric induction and leads further to a nonracemic annulated α,β- butenolide (7). (C) 2000 Elsevier Science Ltd.

Original languageEnglish
Pages (from-to)5583-5587
Number of pages5
JournalTetrahedron Letters
Volume41
Issue number29
DOIs
StatePublished - 15 Jul 2000

Bibliographical note

Funding Information:
The authors wish to thank the US–Israel Science Foundation and the Marcus Center for Pharmaceutical and Medicinal Chemistry at Bar-Ilan University for financial support, and Dr. Hugo E. Gottlieb for his valuable help in NMR analysis.

Keywords

  • Asymmetric induction
  • Butenolides
  • Cyclopentenecarboxylates
  • Lithium ion chelation
  • Michael reactions

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