Development of a solid-phase 'asymmetric resin-capture-release' process: application of an ephedrine chiral resin in an approach to gamma-butyrolactones.
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.
Department of Chemistry, University of Glasgow, The Joseph Black Building, Glasgow, UKG12 8QQ.
Nessan J
NJ
Kerrigan
Panee C
PC
Hutchison
Tom D
TD
Heightman
David J
DJ
Procter
D015107:4-Butyrolactone / Q000138:chemical synthesis* / Q000737:chemistry; D004247:DNA / Q000737:chemistry; D004809:Ephedrine / Q000737:chemistry*; D005069:Evaluation Studies as Topic; D008968:Molecular Conformation; D011108:Polymers / Q000138:chemical synthesis* / Q000737:chemistry; D012117:Resins, Synthetic / Q000737:chemistry*; D013237:Stereoisomerism
D011108:Polymers; D012117:Resins, Synthetic; D004247:DNA; D004809:Ephedrine; D015107:4-Butyrolactone