Tethered aminohydroxylation using acyclic homo-allylic sulfamate esters and sulfonamides as substrates.
Homo-allylic sulfamate esters and sulfonamides are shown to be useful substrates for the tethered aminohydroxylation (TA) reaction. The sulfamate esters undergo the TA reaction delivering 1,2,3-oxathiazinane products whereas the sulfonamides give 1,2-thiazinane products. A range of acyclic homo-allylic sulfamate esters were prepared and subjected to the TA reaction to establish the scope of the process. Nucleophilic ring-opening reactions of the 1,2,3-oxathiazinane products are also described.
Kenworthy
Martin N
MN
Department of Chemistry, University of York, Heslington, York YO10 5DD, UK.
Taylor
Richard J K
RJ
D000605:Amino Alcohols / Q000138:chemical synthesis; D004952:Esters; D005663:Furans / Q000138:chemical synthesis; D006573:Heterocyclic Compounds, 1-Ring / Q000138:chemical synthesis; D008968:Molecular Conformation; D015394:Molecular Structure; D013237:Stereoisomerism; D013449:Sulfonamides / Q000737:chemistry*; D013451:Sulfonic Acids / Q000737:chemistry*; D049971:Thiazides / Q000138:chemical synthesis* / Q000737:chemistry
D000605:Amino Alcohols; D004952:Esters; D005663:Furans; D006573:Heterocyclic Compounds, 1-Ring; D013449:Sulfonamides; D013451:Sulfonic Acids; D049971:Thiazides; C005741:sulfamic acid