Du Bois
et al. have reported the 1,2-diamination reactions of alkenes using a rhodium catalyst. According to their results, aziridines
2 are formed from alkenes and a sulfamide
1 by the
Rh2(esp)2 catalyst and
iodobenzene diacetate-promoted aziridination. By adding sodium iodide, the aziridines
2 are cleaved to form the acyclic intermediate
3 and the consequent ring-closing process affords the 5-membered cyclic sulfamides
4. The given sulfamides
4 are hydrolyzed by an aqueous pyridine and converted to the mono Boc-protected 1,2-diamines. In this synthetic process, the tandem ring-opening and ring-closing reactions proceed involving two S
N2 type substitutions. Therefore, when
E alkenes are used as starting materials,
trans-1,2-diamines are given, and in the case of
Z alkenes,
cis-1,2-diamine derivatives are given, respectively.