The results of the reduction of chiral beta-enamino ketones with sodium borohydride in acetic acid are reported. The reaction is convenient, stereoselective and high yielding and allows the preparation of enantiopure gamma-amino alcohols in syn diastereoselectivity. The reaction is easy to perform and does not require expensive or hazardous chemicals. A mechanistic hypothesis is presented. The absolute configuration of the products obtained is attributed by correlating 1H NMR spectral data with conformational analysis performed by molecular modelling, and confirmed by X-ray analysis.
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Titolo: | Stereoselective synthesis of enantiopure gamma-aminoalcohols by reduction of chiral beta-enaminoketones |
Autori: | |
Data di pubblicazione: | 2006 |
Rivista: | |
Abstract: | The results of the reduction of chiral beta-enamino ketones with sodium borohydride in acetic acid are reported. The reaction is convenient, stereoselective and high yielding and allows the preparation of enantiopure gamma-amino alcohols in syn diastereoselectivity. The reaction is easy to perform and does not require expensive or hazardous chemicals. A mechanistic hypothesis is presented. The absolute configuration of the products obtained is attributed by correlating 1H NMR spectral data with conformational analysis performed by molecular modelling, and confirmed by X-ray analysis. |
Handle: | http://hdl.handle.net/11581/113442 |
Appare nelle tipologie: | Articolo |