Synthesis of Highly Substituted and Enantiomerically Pure 2,3,4-Tris(hydroxyalkyl)pyrrolidines Using a 1,3-Dipolar Cycloaddition Reaction as Key Step

UDRY, GUILLERMO A. OLIVEIRA; REPETTO, EVANGELINA; VEGA, DANIEL R.; VARELA, OSCAR

ChemistrySelect

Wiley

Año: 2017 vol. 2 p. 4774 - 4778

The major endo cycloadducts with a basic structure of methyl1-aryl-3-(benzyl or methyl)-6-menthyloxy-7-oxooctahydropyrano[4,3-c]pyrrole-3-carboxylate were subjected to simple chemicaltransformations (mostly reduction and hydrolysis reactions)to afford pyrrolidine bicyclic systems with varied patterns ofsubstitution and configurations. The cycloadducts have beenobtained by the 1,3-dipolar cycloaddition of (S)-2-menthyloxy-2H-pyran-3(6H)-one, derived from D-xylose, with azomethineylides derived from imines of L-alanine or L-phenylalanine. Thesynthetic route led to enantiomerically pure 2,3,4-tris(hydroxyalkyl)pyrrolidines possessing a tetrasubstituted carbon stereocentervicinal to the ring nitrogen atom and carrying a phenylsubstituent on the other carbon adjacent to the nitrogen.