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cis ‐Dihydroxylation of Olefins by a Non‐Heme Iron Catalyst: A Functional Model for Rieske Dioxygenases
Author(s) -
Chen Kui,
Que, Jr. Lawrence
Publication year - 1999
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/(sici)1521-3773(19990802)38:15<2227::aid-anie2227>3.0.co;2-b
Subject(s) - dihydroxylation , chemistry , ligand (biochemistry) , catalysis , olefin fiber , amine gas treating , stereochemistry , tris , solvent , medicinal chemistry , hydroxylation , enzyme , organic chemistry , biochemistry , enantioselective synthesis , receptor
The first iron complex capable of olefin cis ‐dihydroxylation in combination with H 2 O 2 provides a functional model for Rieske dioxygenases. Mechanistic studies on the model reaction suggest the participation of an Fe III ( η 2 ‐OOH) intermediate, with the oxygen atoms coming exclusively from H 2 O 2 (see reaction scheme; L denotes a tris(6‐methyl‐2‐pyridylmethyl)amine ligand, Solv=solvent). The similarities between the model and the enzymes strengthen the proposal that an Fe III –peroxo intermediate is involved in the enzymatic reactions.