Title
The role of the alcohol and carboxylic acid in directed ruthenium-catalyzed C(sp3)-H <tex>$\alpha$</tex>-alkylation of cyclic aminesThe role of the alcohol and carboxylic acid in directed ruthenium-catalyzed C(sp3)-H <tex>$\alpha$</tex>-alkylation of cyclic amines
Author
Faculty/Department
Faculty of Sciences. Chemistry
Research group
Organic synthesis
Publication type
article
Publication
Weinheim,
Subject
Chemistry
Source (journal)
Chemistry: a European journal. - Weinheim
Volume/pages
18(2012):33, p. 10393-10398
ISSN
0947-6539
ISI
000307108100031
Carrier
E
Target language
English (eng)
Full text (Publishers DOI)
Affiliation
University of Antwerp
Abstract
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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