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Highly Regioselective Palladium‐Catalyzed Carboxylation of Allylic Alcohols with CO 2
Author(s) -
Mita Tsuyoshi,
Higuchi Yuki,
Sato Yoshihiro
Publication year - 2015
Publication title -
chemistry – a european journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.687
H-Index - 242
eISSN - 1521-3765
pISSN - 0947-6539
DOI - 10.1002/chem.201503359
Subject(s) - carboxylation , regioselectivity , transmetalation , allylic rearrangement , catalysis , chemistry , palladium , carboxylic acid , organic chemistry , stoichiometry , medicinal chemistry , isomerization
Various allylic alcohols were carboxylated in the presence of a catalytic amount of PdCl 2 and PPh 3 using ZnEt 2 as a stoichiometric transmetalation agent under a CO 2 atmosphere (1 atm). This carboxylation proceeded in a highly regioselective manner to afford branched carboxylic acids predominantly. The β,γ‐unsaturated carboxylic acid thus obtained was successfully converted into an optically active γ‐butyrolactone, a known intermediate of ( R )‐baclofen.