Sultams aminosulfonic acid

The successful application of sulfanyl amines in the diastereoselective and enantioselective synthesis of as-3,4-disubstituted /3-sultams has been reported (Scheme 56). The protocol is based on the oxidation of the 1,2-aminothiols 178 with hydrogen peroxide and ammonium heptamolybdate. Chlorination of the resulting /3-aminosulfonic acids was achieved using phosgene. The /3-aminosulfonyl chlorides 179 obtained were cyclized under basic conditions and without epimerization to yield the t -3,4-disubstituted /3-sultams 180 (>96% de, ee) (Table 13) <2005S1807>. 

Sultams may be prepared by cydisation of the appropriate aminosulfonic acids and derivatives the ring closure involves nitrogen-sulfur bond formation. The method can be applied to the synthesis of p-sultams, y-sultams and 8-sultams examples are the syntheses of (173) and (174) (Scheme 72). Modifications of the procedure include aminolysis of the corresponding sultones, and oxidation of... 

Sodium hydroxide Sultams from aminosulfonic acid chloride bydrocblorides s. 19,361 NaOH 0... 

Sultams from aminosulfonic acids and reverse reaction s. 11, 364 0... 

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