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Title
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The role of the alcohol and carboxylic acid in directed ruthenium-catalyzed C(sp3)-H -alkylation of cyclic amines
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Author
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Abstract
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| A general directed Ru-catalyzed C(sp3)?H a-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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Language
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English
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Source (journal)
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Chemistry: a European journal. - Weinheim
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Publication
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Weinheim
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2012
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ISSN
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0947-6539
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DOI
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10.1002/CHEM.201201072
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Volume/pages
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18
:33
(2012)
, p. 10393-10398
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ISI
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000307108100031
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Full text (Publisher's DOI)
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