1,2-Cyclic Sulfamidates as Versatile Precursors to Thiomorpholines and Piperazines

1,2-Cyclic Sulfamidates as Versatile Precursors to Thiomorpholines and Piperazines

1,2-Cyclic sulfamidates undergo regiospecific nucleophilic displacement with either methyl thioglycolate or α-amino esters, followed by lactamization (thermal, base-mediated, or cyanide-catalyzed), to give thiomorpholin-3-ones and piperazin-2-ones.

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Veröffentlicht in:Organic letters 2003-03, Vol.5 (6), p.811-814
Hauptverfasser: Williams, Andrew J, Chakthong, Suda, Gray, Diane, Lawrence, Ron M, Gallagher, Timothy
Format: Artikel
Sprache:eng
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Zusammenfassung:1,2-Cyclic sulfamidates undergo regiospecific nucleophilic displacement with either methyl thioglycolate or α-amino esters, followed by lactamization (thermal, base-mediated, or cyanide-catalyzed), to give thiomorpholin-3-ones and piperazin-2-ones.
ISSN:1523-7060
1523-7052
DOI:10.1021/ol027418h