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Direct, Intermolecular, Enantioselective, Iridium-Catalyzed Allylation of Carbamates to Form Carbamate-Protected, Branched Allylic Amines

Daniel J. Weix, Dean Marković, Mitsuhiro Ueda and John F. Hartwig*

*Department of Chemistry, University of Illinois, 600 South Matthews Avenue, Urbana, Illinois 61801, Email: jhartwigillinois.edu

D. J. Weix, D. Marković, M. Ueda, J. F. Hartwig, Org. Lett., 2009, 11, 2944-2947.

DOI: 10.1021/ol901151u (free Supporting Information)


Abstract

A direct reaction between carbamates and achiral allylic carbonates to form branched, conveniently protected primary allylic amines with high regioselectivity and enantioselectivity occurs without base in the presence of a metalacyclic iridium catalyst containing a labile ethylene ligand.

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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, Carbamates


ID: J54-Y2009-2050