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.

Funding

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.

FundersFunder number
Marcus Center for Pharmaceutical and Medicinal Chemistry at Bar-Ilan University
Israel Science Foundation

    Keywords

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

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