Highly Enantioselective Rearrangement of (S)-E-α-p-Tolylsulphinyl-α,β-enolates to (R)-E-γ-Hydroxy-α,β-enoates

DOI: 10.1039/c39860001268

Source and publish data:

Journal of the Chemical Society. Chemical communications p. 1268 - 1270 (1986)

Update date:2022-08-04

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Authors:

Kosugi, Hiroshi

Kitaoka, Masaki

Takahashi, Akira

Uda, Hisashi

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Article abstract of DOI:10.1039/c39860001268

On treatment with pyridine-camphorsulphonic acid, (S)-E-α-p-tolylsulphinyl-α,β-enoates (4) undergo enantioselectively a sequential prototropic shift and allylic sulphoxide-sulphenate rearrangement to produce (R)-E-γ-hydroxy-α,β-enoates (2) in 64-72percent

Full text of DOI:10.1039/c39860001268

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