Controlled Payne rearrangements of 2,3-epoxy alcohols in aprotic media: an enantioselective total synthesis of (+)-exo-brevicomin
- 1 January 1988
- journal article
- Published by Royal Society of Chemistry (RSC) in Journal of the Chemical Society, Chemical Communications
- No. 5,p. 356-358
- https://doi.org/10.1039/c39880000356
Abstract
The catalysis of the isomerisation of primary cis-2,3-epoxy alcohols to threo-1,2-epoxy alcohols by lithium chloride in tetrahydrofuran solution is described; the more reactive terminal epoxides may be selectively trapped in situ by reaction with nucleophiles, and this methodology is used in an enantioselective synthesis of (+)-exo-brevicomin.Keywords
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