Dedicated to the memory of Pr. Ladjama DaifA series of chiral cyclosulfamides have been synthesized by alkaline cyclisation starting from N-benzoylamino acids (Ala, Val, Leu, Phe) derivatives and chlorosulfonyl isocyanate. A simplified and regioselective deprotection of the cyclic compounds (cyclosulfamides) containing the tert-butyloxycarbonyl group (Boc) has been achieved in good yield by fusion under reduced pressure.
pounds. -The preparation of chiral cyclosulfamides (VII) is performed starting from amino esters (I). Benzoylation of (I), followed by reduction and chlorination yield the chiral 1-substituted N-benzyl chloroethylamine hydrochlorides (V). Sulfonylation of (V) by N-Boc sulfamoyl chloride (VI) under alkaline conditions causes spontaneous cyclization into chiral thiadiazolidine dioxides (VII). Regioselective deprotection of the five-membered cyclosulfamides (VII) is achieved by using the fusion method, consisting of heating (VII) in the presence of a catalytic quantity of iodine under reduced pressure. -(NADIA, K.; MALIKA, B.; NAWEL, K.; MEDYAZID, B.; ZINE, R.; AOUF*, N.-E.; J.
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