Biomimetic Hydroxylation of Nonactivated CH2 Groups with Copper Complexes and Molecular Oxygen

Copper(I) complexes with steroidal ligands (see formula) undergo regio‐ and stereoselective γ‐hydroxylation in the 12β‐position of the steroid in the presence of molecular oxygen. After reduction a 17β,12β‐amino alcohol is obtained. Under hydrolytic conditions a 12β‐hydroxy‐17‐ketone can be isolated...

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Published inAngewandte Chemie International Edition Vol. 42; no. 28; pp. 3240 - 3244
Main Authors Schönecker, Bruno, Zheldakova, Tatjana, Liu, Yong, Kötteritzsch, Manuela, Günther, Wolfgang, Görls, Helmar
Format Journal Article
LanguageEnglish
Published Weinheim WILEY-VCH Verlag 21.07.2003
WILEY‐VCH Verlag
Wiley
Subjects
C-H activation
Chemistry
Chemistry, Multidisciplinary
copper
hydroxylations
O-O activation
Physical Sciences
Science & Technology
steroids
CHIRAL LIGANDS
HIGH-PRESSURE
INSERTION
hydroxylation
FUNCTIONAL MODELS
REACTIVITY
O-O activation
DOPAMINE-BETA-HYDROXYLASE
DIOXYGEN COMPLEXES
C-H activation
copper
steroids
INTRAMOLECULAR LIGAND HYDROXYLATION
BINUCLEAR
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Summary:Copper(I) complexes with steroidal ligands (see formula) undergo regio‐ and stereoselective γ‐hydroxylation in the 12β‐position of the steroid in the presence of molecular oxygen. After reduction a 17β,12β‐amino alcohol is obtained. Under hydrolytic conditions a 12β‐hydroxy‐17‐ketone can be isolated.
Bibliography:This research was supported by the Deutsche Forschungsgemeinschaft (SFB 436 "Metallvermittelte Reaktionen nach dem Vorbild der Natur"), the Thuringian Ministerium für Wissenschaft, Forschung und Kunst, and the Fonds der Chemischen Industrie. We thank Schering AG, Berlin, and Jenapharm GmbH & Co. KG, Jena, for providing us with steroids.
ArticleID:ANIE200250815
istex:86DC7098582753681B7F234BC42B9B9457BCE562
ark:/67375/WNG-4PCP8ZN8-F
This research was supported by the Deutsche Forschungsgemeinschaft (SFB 436 “Metallvermittelte Reaktionen nach dem Vorbild der Natur”), the Thuringian Ministerium für Wissenschaft, Forschung und Kunst, and the Fonds der Chemischen Industrie. We thank Schering AG, Berlin, and Jenapharm GmbH & Co. KG, Jena, for providing us with steroids.
ObjectType-Article-1
SourceType-Scholarly Journals-1
ObjectType-Feature-2
content type line 23
ISSN:1433-7851
1521-3773
DOI:10.1002/anie.200250815