Asymmetric Synthesis of 3‐Substituted γ‐ and δ‐Sultams.

Abstract

Thiazine derivatives R 0610Asymmetric Synthesis of 3-Substituted γand δ-Sultams. -A variety of five-and six-membered, optically active sultams is prepared with a view to the biological activities exhibited by sulfonamide derivatives. The synthesis is based on a SAMP-hydrazone methodology. -(ENDERS*, D.; MOLL, A.; BATS, J. W.; Eur.

Parallel Syntheses of Eight-Membered Ring Sultams via Two Cascade Reactions in Water

“…Until now, some powerful synthetic methods for the generation of sultam derivatives have been developed. These routes include several transition metal-catalyzed reactions that afforded sultams, Friedel–Craft reactions, ring-closing metathesis (RCM), cyclizations of aminosulfonyl chlorides, [3 + 2] cycloadditions, both Diels–Alder and Heck reactions, and both intramolecular oxa-Michael and Baylis–Hillman reactions . However, most sultam cyclization reactions above have been carried out in toxic organic solvents and complex procedures are needed to make compound libraries.…”

“…Vinyl sulfonamide is an important type of precursor for making sultams. It embodies a potent Michael acceptor with an electron-deficient double bond, which can be used for many different Michael-addition reactions . Vinyl sulfonamides were prepared by reacting 2-chloroethanesulfonyl chloride with primary amines in DCM containing triethylamine (Scheme ).…”