| The Role of the Alcohol and Carboxylic Acid in Directed Ruthenium-Catalyzed C(sp(3) )H α-Alkylation of Cyclic Amines. | |
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MedLine Citation:
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PMID: 22786664 Owner: NLM Status: Publisher |
Abstract/OtherAbstract:
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A general directed Ru-catalyzed C(sp(3) )H α-alkylation protocol for piperidines (less-reactive substrates than the corresponding five-membered cyclic amines) has been developed. The use of a hindered alcohol (2,4-dimethyl-3-pentanol) as the solvent and catalyst activator, and a catalytic amount of trans-1,2-cyclohexanedicarboxylic acid is necessary to achieve a high conversion to product. This protocol was used to effectively synthesize a number of 2-hexyl- and 2,6-dihexyl piperidines, as well as the alkaloid (±)-solenopsin A. Kinetic studies have revealed that the carboxylic acid additive has a significant effect on catalyst initiation, catalyst longevity, and reverses the reaction selectivity compared with the acid-free reaction (promotes alkylation versus competing alkene reduction). |
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Authors:
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Sheba D Bergman; Thomas E Storr; Hana Prokopcová; Karel Aelvoet; Gaston Diels; Lieven Meerpoel; Bert U W Maes |
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Publication Detail:
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Type: JOURNAL ARTICLE Date: 2012-7-11 |
Journal Detail:
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Title: Chemistry (Weinheim an der Bergstrasse, Germany) Volume: - ISSN: 1521-3765 ISO Abbreviation: - Publication Date: 2012 Jul |
Date Detail:
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Created Date: 2012-7-12 Completed Date: - Revised Date: - |
Medline Journal Info:
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Nlm Unique ID: 9513783 Medline TA: Chemistry Country: - |
Other Details:
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Languages: ENG Pagination: - Citation Subset: - |
Copyright Information:
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Copyright © 2012 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim. |
Affiliation:
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Organic Synthesis, Department of Chemistry, University of Antwerp, Groenenborgerlaan 171, 2020 Antwerp (Belgium), Fax: (+32) 032653233. |
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From MEDLINE®/PubMed®, a database of the U.S. National Library of Medicine
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