Convenient Route to Secondary Sulfinates: Application to the Stereospecific Synthesis of α‑C‑Chiral Sulfonamides

Convenient Route to Secondary Sulfinates: Application to the Stereospecific Synthesis of α‑C‑Chiral Sulfonamides

A convenient synthesis of α-chiral sulfinates from readily available precursors has been accomplished via the corresponding heterocyclic thioethers and sulfones. Treatment of the sulfinates with hydroxylamine sulfonate in aqueous solution provides α-C-chiral primary sulfonamides in good yield (14 ex...

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Veröffentlicht in:Organic letters 2014-12, Vol.16 (23), p.6248-6251
Hauptverfasser: Johnson, Michael G, Gribble, Michael W, Houze, Jonathan B, Paras, Nick A
Format: Artikel
Sprache:eng
Schlagworte:
Catalysis
Molecular Structure
Stereoisomerism
Sulfinic Acids - chemical synthesis
Sulfinic Acids - chemistry
Sulfonamides - chemical synthesis
Sulfonamides - chemistry
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Zusammenfassung:A convenient synthesis of α-chiral sulfinates from readily available precursors has been accomplished via the corresponding heterocyclic thioethers and sulfones. Treatment of the sulfinates with hydroxylamine sulfonate in aqueous solution provides α-C-chiral primary sulfonamides in good yield (14 examples) with retention of stereochemical purity.
ISSN:1523-7060
1523-7052
DOI:10.1021/ol503208z