Tetrahedron: Asymmetry

Asymmetric transfer of nitrenes catalyzed by chiral dirhodium (II) using aromatic sulfamate esters

C Fruit, P Müller

Index: Fruit, Corinne; Mueller, Paul Tetrahedron Asymmetry, 2004 , vol. 15, # 6 p. 1019 - 1026

Full Text: HTML

Citation Number: 80

Abstract

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 ...