Abstract: Starting from the methyl esters of glycine, L-alanine, L-phenylalanine and (S)-2-phenylglycine, we developed a synthetic route to the title compounds in the enantiopure form by means of a stereoselective intramolecular 1,3-dipolar cycloaddition of homochiral nitrilimines 5a-d. Fair to good overall product yields and high cycloaddition diastereoselectivity were obtained.
Stereoselective intramolecular cycloadditions of homochiral nitrilimines as a source of enantiopure 2,3,3a,4,5,6-hexahydro-pyrrolo[3,4-c]pyrazoles / L. De Benassuti, P. Del Buttero, G. Molteni. - In: TETRAHEDRON-ASYMMETRY. - ISSN 0957-4166. - 17:5(2006), pp. 842-845. [10.1016/j.tetasy.2006.02.018]
Stereoselective intramolecular cycloadditions of homochiral nitrilimines as a source of enantiopure 2,3,3a,4,5,6-hexahydro-pyrrolo[3,4-c]pyrazoles
L. De Benassuti;P. Del Buttero;G. Molteni
2006
Abstract
Abstract: Starting from the methyl esters of glycine, L-alanine, L-phenylalanine and (S)-2-phenylglycine, we developed a synthetic route to the title compounds in the enantiopure form by means of a stereoselective intramolecular 1,3-dipolar cycloaddition of homochiral nitrilimines 5a-d. Fair to good overall product yields and high cycloaddition diastereoselectivity were obtained.
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