Tetrahedron Letters p. 2285 - 2288 (1998)
Update date:2022-08-05
Topics:
Luzzio, Frederick A.
Zacherl, DeAnna Piatt
The hydroxylactams obtained from reduction of N-substituted phthalimides were phenylthiated and oxidized to give 3-(phenylsulfonyl)-2,3- dihydroisoindol-1-ones. Deprotonation of the sulfones with sodium hydride followed by treatment with electrophiles gave substitution. Sulfones with suitably-disposed α,β-unsaturated ester groups gave cyclic products from intramolecular Michael addition. Desulfurization of the phenylsulfonyl intermediates was effected in quantitative yield using Raney nickel promoted by ultrasound.
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