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Sequential Catalytic Isomerization and Allylic Substitution. Conversion of Racemic Branched Allylic Carbonates to Enantioenriched Allylic Substitution Products

Shashank Shekhar, Brian Trantow, Andreas Leitner 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

S. Shekhar, B. Trantow, A. Leitner, J. F. Hartwig, J. Am. Chem. Soc., 2006, 128, 11770-11771.

DOI: 10.1021/ja0644273 (free Supporting Information)



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Abstract

Palladium-catalyzed isomerization of readily accessible racemic, branched aromatic allylic esters to terminal allylic esters, followed by sequential iridium-catalyzed allylic substitution, gave branched allylic amines, ethers, and alkyls in good yield with high regioisomeric and enantiomeric selectivity.

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

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


Key Words

Allylamines


ID: J48-Y2006-2980