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

VARDÉ, MARIANA; MARINO, CARLA; REPETTO, EVANGELINA; VARELA, OSCAR

EUROPEAN JOURNAL OF ORGANIC CHEMISTRY

WILEY-V C H VERLAG GMBH

Año: 2022 vol. 2022

1434-193X

1,3-Dipolar cycloadditions of azomethine ylides, prepared from 2,2-dimethoxyacetaldehyde, and enantiomerically pure sugar-derived dihydropyranones led to tetrasubstituted pyrrolidines. The cycloadditions were highly regio-, diastereo- and enantioselective, with the endo approach strongly prevailing. The adducts were subjected to hydrolysis and reductions to afford the target 2,3,4,5-tetrahydroxyalkylpyrrolidines. According to the (R) or (S) stereocenter of the enone, enantiomeric pyrrolidines were obtained