Development of a solid-phase 'asymmetric resin-capture-release' process: application of an ephedrine chiral resin in an approach to gamma-butyrolactones |
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Authors: | Kerrigan Nessan J Hutchison Panee C Heightman Tom D Procter David J |
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Affiliation: | Department of Chemistry, University of Glasgow, The Joseph Black Building, Glasgow, UKG12 8QQ. |
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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 gamma-butyrolactones was selected to illustrate the feasibility of such a process. Alpha,beta-unsaturated esters immobilised on an ephedrine chiral resin have been applied in an asymmetric approach to gamma-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. |
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