The application of the aromatic Mannich reaction to alpha,beta-unsaturated aldehydes, affords a series of new diaminoalkyl naphthols, by a convenient solventless reaction, starting from inexpensive and easily avail-able starting materials. The absolute configurations of the products obtained are attributed on the basis of the coupling constant values of 1H-NMR spectra, joined with the conformational analysis of the molecules by molecular modelling. A mechanistic hypothesis is proposed, which involves an imino–amino intermediate.
Stereoselective synthesis of new vicinal diaminoalkyl naphthols by three component Mannich type reaction of alpha,beta-unsaturated aldehydes
CIMARELLI, Cristina;FRATONI, DAVIDE;PALMIERI, Gianni
2011-01-01
Abstract
The application of the aromatic Mannich reaction to alpha,beta-unsaturated aldehydes, affords a series of new diaminoalkyl naphthols, by a convenient solventless reaction, starting from inexpensive and easily avail-able starting materials. The absolute configurations of the products obtained are attributed on the basis of the coupling constant values of 1H-NMR spectra, joined with the conformational analysis of the molecules by molecular modelling. A mechanistic hypothesis is proposed, which involves an imino–amino intermediate.File in questo prodotto:
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