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Synfacts 2006(12): 1257-1257  
DOI: 10.1055/s-2006-955630
Metal-Catalyzed Asymmetric Synthesis and Stereoselective Reactions
© Georg Thieme Verlag Stuttgart · New York

Pd(0)/Ir(I)-Catalyzed Sequential Allylic Isomerization and Substitution

Contributor(s): Mark Lautens, Andrew Martins
S. Shekhar, B. Tantrow, A. Leitner, J. F. Hartwig*
Yale University, New Haven, USA
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Publikationsverlauf

Publikationsdatum:
22. November 2006 (online)

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Significance

Racemic branched allylic carbo­nates or acetates can be isomerized to the internal alkene using a Pd2(dba)3/PPh3 catalyst. Upon filtration through silical gel to remove Pd, the linear allylic carbonate or ester can be converted into branched allylic substitution products in good yield with excellent ee and branched/linear ratios using an [Ir(cod)Cl]2/phosphoramidite catalyst system. A variety of allylic acetates or carbonates react with diverse nucleophiles to generate numerous chiral allylic amines, ethers, and malo­nates.