A short and stereoselective novel synthesis of benzo[f]chromen-3-amine derivatives in good yields, through a three-component aromatic Betti type reaction under solvent free conditions is reported. The spontaneous reaction occurs in the absence of acid catalysts. The use of chiral 1-phenylethylamine or alpha,beta-unsaturated aldehydes allowed us to prepare enantiopure benzo[f]chromen-3-amine derivatives with good stereoselectivity. Conformational analysis compared with the 1H-NMR data of the products obtained, allowed us to the determine the absolute configuration, which was also confirmed by X-ray analysis.
Novel stereoselective synthesis of 2,3-dihydro-1H-benzo[f]chromen-3-amine derivatives through a one-pot three-component reaction
CIMARELLI, Cristina;FRATONI, DAVIDE;PALMIERI, Gianni
2011-01-01
Abstract
A short and stereoselective novel synthesis of benzo[f]chromen-3-amine derivatives in good yields, through a three-component aromatic Betti type reaction under solvent free conditions is reported. The spontaneous reaction occurs in the absence of acid catalysts. The use of chiral 1-phenylethylamine or alpha,beta-unsaturated aldehydes allowed us to prepare enantiopure benzo[f]chromen-3-amine derivatives with good stereoselectivity. Conformational analysis compared with the 1H-NMR data of the products obtained, allowed us to the determine the absolute configuration, which was also confirmed by X-ray analysis.File in questo prodotto:
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