Covalent Tethers for Precise Amino Alcohol Syntheses: Ring Opening of Epoxides by Pendant Sulfamates and Sulfamides

Covalent Tethers for Precise Amino Alcohol Syntheses: Ring Opening of Epoxides by Pendant Sulfamates and Sulfamides

We describe the development of the first ring opening of epoxides using pendant sulfamates and sulfamides. These reactions are promoted by a base and proceed under mild conditions to afford oxathiazinanes and cyclic sulfamides with excellent diastereoselectivity and regiocontrol. The reactions scale...

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Veröffentlicht in:Organic letters 2023-02, Vol.25 (6), p.982-986
Hauptverfasser: Nagamalla, Someshwar, Mague, Joel T., Sathyamoorthi, Shyam
Format: Artikel
Sprache:eng
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Zusammenfassung:We describe the development of the first ring opening of epoxides using pendant sulfamates and sulfamides. These reactions are promoted by a base and proceed under mild conditions to afford oxathiazinanes and cyclic sulfamides with excellent diastereoselectivity and regiocontrol. The reactions scale well, and the products serve as synthons for ring-opening reactions.
ISSN:1523-7060
1523-7052
1523-7052
DOI:10.1021/acs.orglett.3c00053