General methodology for the preparation of 2,5-disubstituted-1,3-oxazoles.
Deprotonation of 2-(phenylsulfonyl)-1,3-oxazole (1) readily provides a useful C-5 carbanion that is reactive with a variety of electrophiles. Aldehydes and ketones are useful substrates, and the formation of 5-iodo- and 5-tri-n-butylstannyl oxazoles affords access to cross-coupling reactions. Subsequent nucleophilic displacement of the 2-phenylsulfonyl group provides a general route for the synthesis of 2,5-disubstituted-1,3-oxazoles.
Williams
David R
DR
Department of Chemistry, Indiana University, Bloomington, Indiana 47405-7102, USA. williamd@indiana.edu
Fu
Liangfeng
L
D002384:Catalysis; D020650:Combinatorial Chemistry Techniques; D015394:Molecular Structure; D010080:Oxazoles / Q000138:chemical synthesis* / Q000737:chemistry*
D010080:Oxazoles