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Issue 17, 2004
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Development of a solid-phase ‘asymmetric resin-capture–release’ process: application of an ephedrine chiral resin in an approach to γ-butyrolactones

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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 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.

Graphical abstract: Development of a solid-phase ‘asymmetric resin-capture–release’ process: application of an ephedrine chiral resin in an approach to γ-butyrolactones

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Article information


Submitted
11 Jun 2004
Accepted
08 Jul 2004
First published
04 Aug 2004

Org. Biomol. Chem., 2004,2, 2476-2482
Article type
Paper

Development of a solid-phase ‘asymmetric resin-capture–release’ process: application of an ephedrine chiral resin in an approach to γ-butyrolactones

N. J. Kerrigan, P. C. Hutchison, T. D. Heightman and D. J. Procter, Org. Biomol. Chem., 2004, 2, 2476
DOI: 10.1039/B408836K

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