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Synfacts 2006(12): 1257-1257
DOI: 10.1055/s-2006-955630
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
S. Shekhar, B. Tantrow, A. Leitner, J. F. Hartwig*
Yale University, New Haven, USA
Weitere Informationen
Publikationsverlauf
Publikationsdatum:
22. November 2006 (online)
![](https://www.thieme-connect.de/media/synfacts/200612/lookinside/thumbnails/10.1055-s-2006-955630-1.jpg)
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.