Synthesis of sultam scaffolds via intramolecular oxa-Michael and diastereoselective Baylis-Hillman reactions.
A divergent synthetic approach to new sultams utilizing intramolecular oxa-Michael and Baylis-Hillman reactions of readily prepared vinyl sulfonamides and suitably protected amino alcohols, is reported. A variety of seven- and eight-membered ring sultam scaffolds were synthesized using oxa-Michael pathways, whereas both five- and six-membered rings were synthesized using Baylis-Hillman methods. Baylis-Hillman reactions proceed with good to excellent levels of diastereoselectivity, and oxa-Michael reactions leading to eight-membered ring sultams provide empirical evidence validating 8- endo-trig cyclization pathways.
Department of Chemistry, University of Kansas, Lawrence, Kansas 66045-7582, USA.
Aihua
A
Zhou
Paul R
PR
Hanson
D002384:Catalysis; D020650:Combinatorial Chemistry Techniques; D003500:Cyclization; D015394:Molecular Structure; D013237:Stereoisomerism; D013449:Sulfonamides / Q000138:chemical synthesis* / Q000737:chemistry
D013449:Sulfonamides; C480101:beta-sultam