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A Versatile Hexadiene Synthesis by Decarboxylative sp 3 –sp 3 Coupling/Cope Rearrangement
Author(s) -
Waetzig Shelli R.,
Rayabarapu Dinesh K.,
Weaver Jimmie D.,
Tunge Jon A.
Publication year - 2006
Publication title -
angewandte chemie international edition
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 1433-7851
DOI - 10.1002/anie.200600721
Subject(s) - coupling (piping) , tandem , decarboxylation , chemistry , structural isomer , coupling reaction , catalysis , medicinal chemistry , stereochemistry , combinatorial chemistry , organic chemistry , materials science , metallurgy , composite material
Have it both ways : The palladium‐catalyzed decarboxylative coupling of esters with two allyl groups results in kinetic allylation at a position α to electron‐withdrawing groups. Tandem allylation/Cope rearrangement provides access to γ‐coupling products (see scheme). Thus, the desired regioisomer is obtained simply by controlling the temperature of the reaction mixture.