Sulfamidation of 2-arylaldehydes and ketones with chloramine-T.
[reaction: see text] A series of aliphatic and aromatic carbonyl compounds has been transformed into the corresponding sulfamidated products by means of amine-catalyzed nitrene transfer of chloramine-T. Depending on the residues R, either alpha-sulfamidation in the case of aromatic aldehydes and acetone derivatives or direct sulfamidation at the carbonyl functionality of aliphatic aldehydes has been observed. Applying microwave conditions, good to excellent yields under significantly reduced reaction times could be obtained, thus providing a facile access to alpha,alpha-disubstituted amino acids.
Baumann
Thomas
T
Institut für Organische Chemie, Universität Karlsruhe (TH), Fritz-Haber-Weg 6, D-76131 Karlsruhe, Germany.
Bächle
Michael
M
Bräse
Stefan
S
D000447:Aldehydes / Q000138:chemical synthesis*; D000586:Amination; D000596:Amino Acids / Q000138:chemical synthesis* / Q000737:chemistry; D002384:Catalysis; D002700:Chloramines / Q000737:chemistry*; D007659:Ketones / Q000737:chemistry*; D015394:Molecular Structure; D013237:Stereoisomerism; D013457:Sulfur Compounds / Q000737:chemistry; D014105:Tosyl Compounds / Q000737:chemistry*
D000447:Aldehydes; D000596:Amino Acids; D002700:Chloramines; D007659:Ketones; D013457:Sulfur Compounds; D014105:Tosyl Compounds; C016300:chloramine-T