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Palladium‐Catalyzed Selective Anti ‐ Markovnikov Oxidation of Allylic Esters
Author(s) -
Dong Jia Jia,
FañanásMastral Martín,
Alsters Paul L.,
Browne Wesley R.,
Feringa Ben L.
Publication year - 2013
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.201301809
Subject(s) - allylic rearrangement , chemistry , aldol reaction , isomerization , markovnikov's rule , regioselectivity , palladium , catalysis , aldehyde , organic chemistry , combinatorial chemistry
An aldol alternative : The palladium(II)‐catalyzed anti‐Markovnikov oxidation of allylic esters to aldehydes at room temperature provides a viable alternative to valuable cross aldol products. High regioselectivity towards the aldehyde product was achieved using the ester protecting group for the allylic alcohol. Rapid isomerization and the much higher rate of oxidation of the branched isomer result in the same product forming from both linear and branched allylic esters.