Application

No.106
A Soft Nucleophile for Palladium(0)-Catalyzed
Addition to Allylic Systems
P1353 Methyl Phenylsulfonylacetate (1) 5g

The product 1 reacts with allylic acetate 2 as a soft nucleophile in the presence of a palladium(0) catalyst and afford 2-phenylsulfonyl (4E)-enoate 3, which followed by desulfonation leads to the construction of trans-4-enoate 4.

References

1) A stereocontrolled synthesis of trans-allylic amines
W. J. Thompson, T. J. Tucker, J. E. Schwering, J. L. Barnes, Tetrahedron Lett., 31, 6819 (1990).
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