Synfacts 2010(10): 1163-1163  
DOI: 10.1055/s-0030-1258643
Metal-Catalyzed Asymmetric Synthesis and Stereoselective Reactions
© Georg Thieme Verlag Stuttgart ˙ New York

Kinetic Asymmetric Substitution of Racemic Allylic Esters

Contributor(s): Mark Lautens, Stephen G. Newman
L. M. Stanley, C. Bai, M. Ueda, J. F. Hartwig*
University of Illinois, Urbana, USA
Further Information

Publication History

Publication Date:
22 September 2010 (online)

Significance

Asymmetric allylic substitution of linear allylic carbonates is a useful, well-developed process. Substitutions starting from the chiral, racemic branched starting materials are less established, despite their availability and typically higher reactivity. Utilizing their previously developed iridium-phosphoramidite complex, the authors describe highly enantioselective kinetic asymmetric substitution reactions of branched allylic benz­oates. A diverse range of carbon and heteroatom nucleophiles can be used.