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Synfacts 2006(2): 0146-0146
DOI: 10.1055/s-2005-924780
DOI: 10.1055/s-2005-924780
Metal-Catalyzed Asymmetric Synthesis and Stereoselective Reactions
© Georg Thieme Verlag Stuttgart · New York
Regioselective Heck Couplings of α,β-Unsaturated Tosylates and Mesylates
A. L. Hansen, T. Skrydstrup*
University of Aarhus, Denmark
Weitere Informationen
Publikationsverlauf
Publikationsdatum:
23. Januar 2006 (online)
Significance
Heck couplings of α,b-unsaturated tosylates and mesylates with N-acyl-N-vinylamines and vinyl ethers were highly regioselective for the α-position using Pd2(dba)3 and DPPF. This method provides a cheaper alternative to the use of toxic triflates. In all cases the regioselectivity was greater than 19:1 (branched:linear). Disubstituted amides did not react with either the mesylates or tosylates suggesting that the monosubstituted amide functionality plays an important role.