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 in	Angewandte 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
Language	English
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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Abstract	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.
AbstractList	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.
Author	Kötteritzsch, Manuela Günther, Wolfgang Zheldakova, Tatjana Görls, Helmar Liu, Yong Schönecker, Bruno
Author_xml	– sequence: 1 givenname: Bruno surname: Schönecker fullname: Schönecker, Bruno email: c8scbr@uni-jena.de organization: Institut für Organische Chemie und Makromolekulare Chemie, Friedrich-Schiller-Universität Jena, Lessingstrasse 8, 07743 Jena, Germany, Fax: (+49) 3641-948292 – sequence: 2 givenname: Tatjana surname: Zheldakova fullname: Zheldakova, Tatjana organization: Institute for Bioorganic Chemistry , Belorussian National Academy of Sciences, Minsk (Belorussia) – sequence: 3 givenname: Yong surname: Liu fullname: Liu, Yong organization: Institut für Organische Chemie und Makromolekulare Chemie, Friedrich-Schiller-Universität Jena, Lessingstrasse 8, 07743 Jena, Germany, Fax: (+49) 3641-948292 – sequence: 4 givenname: Manuela surname: Kötteritzsch fullname: Kötteritzsch, Manuela organization: Institut für Organische Chemie und Makromolekulare Chemie, Friedrich-Schiller-Universität Jena, Lessingstrasse 8, 07743 Jena, Germany, Fax: (+49) 3641-948292 – sequence: 5 givenname: Wolfgang surname: Günther fullname: Günther, Wolfgang organization: Institut für Organische Chemie und Makromolekulare Chemie, Friedrich-Schiller-Universität Jena, Lessingstrasse 8, 07743 Jena, Germany, Fax: (+49) 3641-948292 – sequence: 6 givenname: Helmar surname: Görls fullname: Görls, Helmar organization: Institut für Anorganische und Analytische Chemie, Friedrich-Schiller-Universität Jena, Lessingstrasse 8, 07743 Jena, Germany
BackLink	https://www.ncbi.nlm.nih.gov/pubmed/12876732$$D View this record in MEDLINE/PubMed
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Cites_doi	10.1021/CR400327T 10.1021/ja026047x 10.1021/ja015702i 10.1021/ja0125265 10.1002/(ISSN)1521-3757
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Keywords	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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Notes	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
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Snippet	Copper(I) complexes with steroidal ligands (see formula) undergo regio‐ and stereoselective γ‐hydroxylation in the 12β‐position of the steroid in the presence...
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SubjectTerms	C-H activation Chemistry Chemistry, Multidisciplinary copper hydroxylations O-O activation Physical Sciences Science & Technology steroids
Title	Biomimetic Hydroxylation of Nonactivated CH2 Groups with Copper Complexes and Molecular Oxygen
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