Beilstein J. Org. Chem.2015,11, 622–627, doi:10.3762/bjoc.11.70
purification of enamines 1a–i. One of the main modifications made to the synthetic procedure is at the end of the reaction, wet diethyl ether was added in order to precipitate all titaniumsalts (this strategy was previously used after formation of imine bonds using TiCl4) [16]. Enamine 1g was more stable than
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Graphical Abstract
Scheme 1:
Synthesis of enamines from ketones with percentage yields.
Beilstein J. Org. Chem.2015,11, 66–73, doi:10.3762/bjoc.11.10
: aminoalcohols; free-radical addition; imine; multicomponent reaction; titaniumsalts; Introduction
Multicomponent reactions (MCRs) represent a green approach towards the synthesis of polyfunctionalized molecules by promoting multiple bond-forming mechanisms in a one-pot synthesis [1][2][3][4][5][6][7
our ongoing investigation of the role of titaniumsalts in mediating selective radical transformations [13][14], we have developed new, simple protocols for the synthesis of complex organic compounds through nucleophilic radical addition to imines generated in situ [15]. Several recent contributions
approach. In fact, our procedure requires neither the preformation of imines nor anhydrous media, due to the coordinating effect of titaniumsalts, which promote the one-pot synthesis of amino derivatives according to a classical MCR.
The basic approach consists of the simple mixing of an aniline, an
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Graphical Abstract
Scheme 1:
Nucleophilic radical addition to imines mediated by titanium salts.