New approaches in asymmetric synthesis using y-alkoxybutenolides

B.L. Feringa*, B de Lange, J.F.G.A. Jansen, J.C. de Jong, M. Lubben, W. Faber, E.P. Schudde

*Corresponding author for this work

    Research output: Contribution to journalArticleAcademicpeer-review

    Abstract

    The synthesis of a new class of auxiliary based chiral synthons, gamma-alkoxy-2(5H)-furanones, is described. The multifunctional compounds enter a variety of asymmetric transformations leading to acyclic- and cyclic-products with up to four new stereogenic centers in a single operation with stereoselectivities exceeding 98%. Applications in new routes to an enantiomerically pure beta-lactam and lignans are given.

    Original languageEnglish
    Pages (from-to)1865-1871
    Number of pages7
    JournalPure and Applied Chemistry
    Volume64
    Issue number12
    Publication statusPublished - Dec-1992
    Event9TH INTERNATIONAL CONF ON ORGANIC SYNTHESIS - , Canada
    Duration: 28-Jun-19922-Jul-1992

    Keywords

    • ENANTIOSELECTIVE SYNTHESIS
    • 1,4-ADDITIONS
    • MENTHYLOXYBUTENOLIDES
    • 5-ALKOXY-2(5H)-FURANONES
    • ADDITIONS

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