Journal of Organic Chemistry p. 4669 - 4681 (1983)
Update date:2022-08-04
Topics:
Tamaru, Yoshinao
Yamada, Yoshimi
Kagotani, Masahiro
Ochiai, Hirofumi
Nakajo, Eiji
et al.
The combination of a sulfonylpalladation of acyclic dienes 1 (with 2 equiv of NaSO2R and 1 equiv of PdCl2 in acetic acid or acetic acid-H2O at 50-80 deg C under air) and a protiodepalladation of the thus obtained <1-(sulfonylmethyl)-?-allyl>palladium complexes 3 with dimethylglyoxime (in a protic solvent at room temperature) provides di- and trisubstituted (Z)-Δ3-sulfones 12 selectively, irrespective of the stereochemistry of the starting dienes.Similar treatment of 1-vinylcycloalkenes 5 (n (1,3) strain between Pd and the substituent on the allylic position.
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