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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)


Abstract

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



Enantioselective Iridium-Catalyzed Allylic Amination of Ammonia and Convenient Ammonia Surrogates

M. J. Pouy, A. Leitner, D. J. Weix, S. Ueno, J. F. Hartwig, Org. Lett., 2007, 9, 3949-3952.


Key Words

Allylic Amines


ID: J48-Y2002-1390