Regio- and Enantioselective Allylic Amination of Achiral Allylic Esters Catalyzed by an Iridium-Phosphoramidite Complex
Toshimichi Ohmura and John F. Hartwig*
*Department of Chemistry, Yale University, P.O. Box 208107, New Haven, Connecticut 06520-8107, Email: john.hartwigyale.edu
T. Ohmura, J. F. Hartwig, J. Am. Chem. Soc., 2002, 124, 15164-15165.
DOI: 10.1021/ja028614m (free Supporting Information)
An iridium-catalyzed enantioselective allylic amination of (E)-cinnamyl and terminal aliphatic allylic carbonates using chiral phosphoramidites as ligands provided branched secondary and tertiary allylic amines in high yields with excellent regio- and enantioselectivity. Reactions in THF displayed the most suitable balance of rate and enantioselectivity.
see article for more examples and reactions
M. J. Pouy, A. Leitner, D. J. Weix, S. Ueno, J. F. Hartwig, Org. Lett., 2007, 9, 3949-3952.