Iridium(I)-catalyzed regio- and enantioselective decarboxylative allylic amidation

ORGN 130

Om V Singh, omvir.singh@utsa.edu and Hyunsoo Han, hyunsoo.han@utsa.edu. Department of Chemistry, The University of Texas at San Antonio, 6900 N Loop 1604 West, San Antonio, TX 78249
Iridium-catalyzed decarboxylative allylic amidation of 1 will be presented. The reactions require Ir(I), phosphoramidite ligand, and DBU as well as proton sponge which is crucial for the catalytic reaction, and proceed with excellent regio- and enantioselectivities to afford the branched 1-(aryl/alkyl)-1-benzyloxycarbonylaminoprop-2-ene 2 in good to excellent yields. The scope, mechanism, and synthetic application of the reactions will be discussed.

 

Asymmetric Reactions and Syntheses, Metal-Mediated Reactions, Combinatorial, Parallel, and Solid-Phase Chemistry
8:00 PM-10:00 PM, Sunday, 10 September 2006 Moscone Center -- Hall D, Poster

Division of Organic Chemistry

The 232nd ACS National Meeting, San Francisco, CA, September 10-14, 2006