Development of a solid-phase 'asymmetric resin-capture-release' process: Application of an ephedrine chiral resin in an approach to γ- butyrolactonest

Nessan J. Kerrigan, Panee C. Hutchison, Tom D. Heightman, David J. Procter

    Research output: Contribution to journalArticlepeer-review

    Abstract

    The potential of a solid-phase asymmetric resin-capture-release strategy for high-throughput synthesis has been evaluated. Fukuzawa's Sm(II)-mediated, asymmetric approach to γ-butyrolactones was selected to illustrate the feasibility of such a process. α,β-Unsaturated esters immobilised on an ephedrine chiral resin have been applied in an asymmetric approach to γ-butyrolactones. Lactone products are obtained in moderate isolated yields with selectivities up to 96% ee. In addition, we have shown that the ephedrine resin can be conveniently recovered and recycled although in some cases lower yields were obtained on reuse of the chiral resin. A short synthesis of a moderate DNA-binding microbial metabolite using asymmetric resin-capture-release is also described.
    Original languageEnglish
    Pages (from-to)2476-2482
    Number of pages6
    JournalOrganic and Biomolecular Chemistry
    Volume2
    Issue number17
    DOIs
    Publication statusPublished - 7 Sep 2004

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