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Catalytic Epoxidation and 1,2‐Dihydroxylation of Olefins with Bispidine–Iron( II )/H 2 O 2 Systems
Author(s) -
Bukowski Michael R.,
Comba Peter,
Lienke Achim,
Limberg Christian,
Lopez de Laorden Carlos,
MasBallesté Rubén,
Merz Michael,
Que Lawrence
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.200504357
Subject(s) - dihydroxylation , catalysis , chemistry , stereochemistry , organic chemistry , enantioselective synthesis
Going ferryl : Fe II complexes with two isomeric bispidine ligands catalyze the oxidation of cyclooctene with H 2 O 2 in MeCN under aerobic conditions with high selectivity for the epoxide (see scheme; L=bispidine ligand). An {Fe IV O} complex is postulated to be the oxidant, formed by the homolytic cleavage of the OO bond of an {Fe III ‐OOH} intermediate. Performing the reaction under argon gives a mixture of cis and trans diols as well as the epoxide.