Asymmetric transfer of nitrenes catalyzed by chiral dirhodium(II) using aromatic sulfamate esters
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 [Rh 2{(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.
Fruit, Corinne,Mueller, Paul
p. 1019 - 1026
(2007/10/03)
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