Intramolecular oxa-Michael and Baylis Hillman Strategies towards Sultam Libraries

Abstract

The utilization of Baylis-Hillman and oxa-Michael methodologies for the synthesis of sultam (cyclic sulfonamides) libraries from chiral non-racemic amino alcohols and epoxides is reported. These strategies employ a divergent synthetic approach utilizing a central vinyl sulfonamide linchpin and a variety of functional group pairing reactions to generate skeletally diverse sultam scaffolds with a variety of functionalizable handles. A variety of 5, 6, 7, and 8-member sultams are accessible through these methods with excellent diastereoselectivity, yields, and purities. In addition, the oxa-Michael protocol has been utilized in a one-pot protocol for the synthesis of alibrary of 4,4-dioxo-1,4,5-oxathiazepines.