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.
Stereoselective synthesis of enantiopure gamma-aminoalcohols by reduction of chiral beta-enaminoketones
CIMARELLI, Cristina;GIULI, Sandra;PALMIERI, Gianni
2006-01-01
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.File in questo prodotto:
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