Diastereoselective synthesis of enantioenriched homopropargyl amino alcohols from α-dibenzylamino aldehydes and their use as chiral synthons |
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Authors: | José M Andrés Alfonso Pérez-Encabo María Ramírez |
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Institution: | Departamento de Química Orgánica, Facultad de Ciencias, Universidad de Valladolid, Doctor Mergelina s/n, 47011-Valladolid, Spain |
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Abstract: | Homochiral α-dibenzylamino aldehydes, prepared from the corresponding α-amino acids, react with propargyl bromide and zinc in DMF/THF (1:1) or DMF/Et2O (1:1) at 20 °C to afford, in good yields and dr, homopropargylic 1,2-amino alcohols. anti Diastereomers were always formed as major products in this reaction. These compounds are versatile intermediates for a variety of synthetic targets: γ-amino-β-hydroxy-ketones, 4-amino-1,3-diols, 1,7-diamino-2,6-diols, and ω-amino-δ-hydroxy esters. |
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Keywords: | Propargylation Amino acids Amino aldehydes Asymmetric synthesis Zinc |
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