Enantioselective Synthesis of 2,3,4,5-Tetra(hydroxyalkyl)pyrrolidines through 1,3-Dipolar Cycloadditions

Artículo

Autoría

VARDE, MARIANA ; MARINO, MARIA CARLA ; REPETTO, EVANGELINA ; VARELA, OSCAR JOSE

Fecha

2022

Editorial y Lugar de Edición

WILEY-V C H VERLAG GMBH

Revista

EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, vol. 2022 (pp. 1-8) WILEY-V C H VERLAG GMBH

Resumen Información suministrada por el agente en SIGEVA

1,3-Dipolar cycloadditions were conducted starting from azomethine ylides and enantiomerically pure sugar-derived dihydropyranones. The ylide intermediates were generated from imines obtained by condensation of glycine or L-alanine esters and 2,2-dimethoxyacetaldehyde. This aldehyde was employed as precursor of a dimethoxymethyl group attached to the pyrrolidine ring, instead of the usual aryl group derived from aromatic aldehydes. Under silver catalysis the cycloaddition was highly regio- and ... 1,3-Dipolar cycloadditions were conducted starting from azomethine ylides and enantiomerically pure sugar-derived dihydropyranones. The ylide intermediates were generated from imines obtained by condensation of glycine or L-alanine esters and 2,2-dimethoxyacetaldehyde. This aldehyde was employed as precursor of a dimethoxymethyl group attached to the pyrrolidine ring, instead of the usual aryl group derived from aromatic aldehydes. Under silver catalysis the cycloaddition was highly regio- and diastereoselective, affording good yields of the 2,5-cis cycloadducts, with the endo configuration strongly prevailing. The enantioselectivity was controlled by the acetal stereocenter of the pyranone: the (S)-isomer gave a pyrrolidine with a defined configuration for the four asymmetric ring carbons, while the (R)-dihydropyranone gave the enantiomeric ring. A sequence of reactions applied to the cycloadducts derived from (S)-enone afforded the target 2,3,4,5-tetra(hydroxyalkyl)pyrrolidines. The enantiomers were obtained from cycloadducts synthesized from the (R)-enone. The pyrrolidines were evaluated as inhibitors of the ?-galactofuranosidase from Penicillium fellutanum.

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Palabras Clave

ENZYME INHIBITONAZOMETHINE YLIDE1,3-DIPOLAR CYCLOADDITIONSUGAR ENONEHYDROXYPYRROLIDINE

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http://hdl.handle.net/11336/212772