P. Schwenkkraus et Hh. Otto, PROPERTIES AND REACTIONS OF SUBSTITUTED 1,2-THIAZETIDINE 1,1-DIOXIDES- C-3 SUBSTITUTED BETA-SULTAMS, Archiv der pharmazie, 326(9), 1993, pp. 519-523
(RS)-3-(2-Chloroethyl)-beta-sultam (6) is obtained from methyl 4-bromo
crotonate (1) by a five step synthesis. The analogous (R)-3-chlorometh
yl-beta-sultam (12) is available from (R)-benzylcysteinol (9). While t
he chlorine in 6 is replaced easily by iodine yielding 7, the analogou
s reaction with 12 fails. The 3-(hydroxyethyl/methyl) substituted beta
-sultams 17 and 21 are prepared by similar routes. All structures are
established by spectroscopic