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A Simple Iridium Catalyst with a Single Resolved Stereocenter for Enantioselective Allylic Amination. Catalyst Selection from Mechanistic Analysis

Andreas Leitner, Shashank Shekhar, Mark J. Pouy and John F. Hartwig*

*Department of Chemistry, University of Illinois at Urbana-Champaign, A410 Chemical and Life Sciences Laboratory, 600 S Mathews, Urbana, IL 61801, Email: jhartwiguiuc.edu

A. Leitner, S. Shekhar, M. J. Pouy, J. F. Hartwig, J. Am. Chem. Soc., 2005, 127, 15506-15514.

DOI: 10.1021/ja054331t (free Supporting Information)



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Abstract

Iridium catalysts derived from a phosphoramidite containing a biphenolate group, one distal chiral substituent at nitrogen and a large achiral cycloalkyl group were shown to react in all cases examined with nearly the same rates, regioselectivities, and enantioselectivities as catalysts derived from the previously reported, more elaborate ligands.

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Key Words

Allylamines


ID: J48-Y2005-2690