Highly enantioselective rearrangement of (S)-E-α-p-tolysulphinyl-α,β-enoates to (R)-E-γ-hydroxy-α,β-enoates
- 1 January 1986
- journal article
- research article
- Published by Royal Society of Chemistry (RSC) in Journal of the Chemical Society, Chemical Communications
- No. 16,p. 1268-1270
- https://doi.org/10.1039/c39860001268
Abstract
On treatment with pyridine–camphorsulphonic acid, (S)-E-α-p-tolysulphinyl-α-β-enoates (4) undergo enantio-selectively a sequential prototropic shift and allylic sulphoxide–sulphenate rearrangement to produce (R)-E-γ-hydroxy-α,β-enoates (2) in 64–72% optical purity.Keywords
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