176. C. Fruit, P. Müller,
     “Asymmetric transfer of nitrenes catalyzed by chiral dirhodium(II) using aromatic sulfamate esters”
     Tetrahedron: Asymmetry 2004, 15, 1019-1026.

Enantioselective intra- and intermolecular insertions of aromatic sulfamate esters into activated C–H bonds have been achieved via in situ generated phenyliodinanes in the presence of PhI(OAc)₂, MgO, and chiral Rh(II) catalysts. The optimal results were obtained with [Rh₂{(S)-nttl}₄] and [Rh₂{(R)-ntv}₄] as catalysts with up to 52% ee. In contrast, phenylsulfamates with allylic ortho-substituents reacted via intramolecular aziridination rather than insertion. The intermolecular amidation of indane proceeded with up to 97% yield when the reaction was carried out with the sulfamate in excess.

DOI : 10.1016/j.tetasy.2004.01.015