Tetrahedron Letters p. 3105 - 3108 (1999)
Update date:2022-08-05
Topics:
Evans, P. Andrew
Brandt, Thomas A.
Robinson, John E.
Palladium-catalyzed rearrangement of the deuterium labeled vinylogous carbonate 1 furnished the β-formyl esters 3a/b in 68% yield, while the Z- vinylogous sulfonate (Z-VINS) 2 under analogous reaction conditions led to reversible O-alkylation and isomerization to afford the E-VINS 4a/b in 61% yield. This observation prompted the development of the vinylogous sulfonate as an improved leaving group for a variety of palladium-catalyzed allyIic substitution reactions.
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