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Synfacts 2007(4): 0406-0406
DOI: 10.1055/s-2007-968335
DOI: 10.1055/s-2007-968335
Metal-Catalyzed Asymmetric Synthesis and Stereoselective Reactions
© Georg Thieme Verlag Stuttgart · New York
Iridium(I)-Catalyzed Decarboxylative Allylic Amidation
O. V. Singh, H. Han*
The University of Texas at San Antonio, USA
Further Information
Publication History
Publication Date:
23 March 2007 (online)
![](https://www.thieme-connect.de/media/synfacts/200704/lookinside/thumbnails/10.1055-s-2007-968335-1.jpg)
Significance
The first Ir(I)-catalyzed regio- and enantioselective decarboxylative allylic amidation of substituted allyl benzyl imidodicarbonates is accomplished using [Ir(cod)Cl]2 and a phosphoramidite ligand. The reaction has a broad scope including linear and branched alkyl, conjugated and isolated alkenyl, as well as aryl and heteroaryl substituents on the olefin. Good to excellent yields and high enantioselectivities are seen under mild reaction conditions. The synthetic utility of the products is demonstrated by allylation and subsequent ring-closing metathesis to produce a 2,5-dihydropyrrole, and by performing an intramolecular amidomercuration to produce a synthetic precursor to (+)-isosolenopsin A.