Synthesis of Highly Substituted and Enantiomerically Pure 2,3,4-Tris(hydroxyalkyl)pyrrolidines Using a 1,3-Dipolar Cycloaddition Reaction as Key Step
The major endo cycloadducts with a basic structure of methyl 1-aryl-3-(benzyl or methyl)-6-menthyloxy-7-oxooctahydropyrano[4,3-c]pyrrole-3-carboxylate were subjected to simple chemical transformations (mostly reduction and hydrolysis reactions) to afford pyrrolidine bicyclic systems with varied patt...
Guardado en:
| Autores principales: | , , , |
|---|---|
| Formato: | JOUR |
| Materias: | |
| Acceso en línea: | http://hdl.handle.net/20.500.12110/paper_23656549_v2_n17_p4774_Udry |
| Aporte de: |
| id |
todo:paper_23656549_v2_n17_p4774_Udry |
|---|---|
| record_format |
dspace |
| spelling |
todo:paper_23656549_v2_n17_p4774_Udry2023-10-03T16:41:16Z Synthesis of Highly Substituted and Enantiomerically Pure 2,3,4-Tris(hydroxyalkyl)pyrrolidines Using a 1,3-Dipolar Cycloaddition Reaction as Key Step Udry, G.A.O. Repetto, E. Vega, D.R. Varela, O. 1,3-dipolar-cycloaddition azomethine ylide polyhydroxyalkylpyrrolidine pyrrolidine sugar enone The major endo cycloadducts with a basic structure of methyl 1-aryl-3-(benzyl or methyl)-6-menthyloxy-7-oxooctahydropyrano[4,3-c]pyrrole-3-carboxylate were subjected to simple chemical transformations (mostly reduction and hydrolysis reactions) to afford pyrrolidine bicyclic systems with varied patterns of substitution and configurations. The cycloadducts have been obtained by the 1,3-dipolar cycloaddition of (S)-2-menthyloxy-2H-pyran-3(6H)-one, derived from D-xylose, with azomethine ylides derived from imines of L-alanine or L-phenylalanine. The synthetic route led to enantiomerically pure 2,3,4-tris(hydroxyalkyl) pyrrolidines possessing a tetrasubstituted carbon stereocenter vicinal to the ring nitrogen atom and carrying a phenyl substituent on the other carbon adjacent to the nitrogen. © 2017 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim JOUR info:eu-repo/semantics/openAccess http://creativecommons.org/licenses/by/2.5/ar http://hdl.handle.net/20.500.12110/paper_23656549_v2_n17_p4774_Udry |
| institution |
Universidad de Buenos Aires |
| institution_str |
I-28 |
| repository_str |
R-134 |
| collection |
Biblioteca Digital - Facultad de Ciencias Exactas y Naturales (UBA) |
| topic |
1,3-dipolar-cycloaddition azomethine ylide polyhydroxyalkylpyrrolidine pyrrolidine sugar enone |
| spellingShingle |
1,3-dipolar-cycloaddition azomethine ylide polyhydroxyalkylpyrrolidine pyrrolidine sugar enone Udry, G.A.O. Repetto, E. Vega, D.R. Varela, O. Synthesis of Highly Substituted and Enantiomerically Pure 2,3,4-Tris(hydroxyalkyl)pyrrolidines Using a 1,3-Dipolar Cycloaddition Reaction as Key Step |
| topic_facet |
1,3-dipolar-cycloaddition azomethine ylide polyhydroxyalkylpyrrolidine pyrrolidine sugar enone |
| description |
The major endo cycloadducts with a basic structure of methyl 1-aryl-3-(benzyl or methyl)-6-menthyloxy-7-oxooctahydropyrano[4,3-c]pyrrole-3-carboxylate were subjected to simple chemical transformations (mostly reduction and hydrolysis reactions) to afford pyrrolidine bicyclic systems with varied patterns of substitution and configurations. The cycloadducts have been obtained by the 1,3-dipolar cycloaddition of (S)-2-menthyloxy-2H-pyran-3(6H)-one, derived from D-xylose, with azomethine ylides derived from imines of L-alanine or L-phenylalanine. The synthetic route led to enantiomerically pure 2,3,4-tris(hydroxyalkyl) pyrrolidines possessing a tetrasubstituted carbon stereocenter vicinal to the ring nitrogen atom and carrying a phenyl substituent on the other carbon adjacent to the nitrogen. © 2017 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim |
| format |
JOUR |
| author |
Udry, G.A.O. Repetto, E. Vega, D.R. Varela, O. |
| author_facet |
Udry, G.A.O. Repetto, E. Vega, D.R. Varela, O. |
| author_sort |
Udry, G.A.O. |
| title |
Synthesis of Highly Substituted and Enantiomerically Pure 2,3,4-Tris(hydroxyalkyl)pyrrolidines Using a 1,3-Dipolar Cycloaddition Reaction as Key Step |
| title_short |
Synthesis of Highly Substituted and Enantiomerically Pure 2,3,4-Tris(hydroxyalkyl)pyrrolidines Using a 1,3-Dipolar Cycloaddition Reaction as Key Step |
| title_full |
Synthesis of Highly Substituted and Enantiomerically Pure 2,3,4-Tris(hydroxyalkyl)pyrrolidines Using a 1,3-Dipolar Cycloaddition Reaction as Key Step |
| title_fullStr |
Synthesis of Highly Substituted and Enantiomerically Pure 2,3,4-Tris(hydroxyalkyl)pyrrolidines Using a 1,3-Dipolar Cycloaddition Reaction as Key Step |
| title_full_unstemmed |
Synthesis of Highly Substituted and Enantiomerically Pure 2,3,4-Tris(hydroxyalkyl)pyrrolidines Using a 1,3-Dipolar Cycloaddition Reaction as Key Step |
| title_sort |
synthesis of highly substituted and enantiomerically pure 2,3,4-tris(hydroxyalkyl)pyrrolidines using a 1,3-dipolar cycloaddition reaction as key step |
| url |
http://hdl.handle.net/20.500.12110/paper_23656549_v2_n17_p4774_Udry |
| work_keys_str_mv |
AT udrygao synthesisofhighlysubstitutedandenantiomericallypure234trishydroxyalkylpyrrolidinesusinga13dipolarcycloadditionreactionaskeystep AT repettoe synthesisofhighlysubstitutedandenantiomericallypure234trishydroxyalkylpyrrolidinesusinga13dipolarcycloadditionreactionaskeystep AT vegadr synthesisofhighlysubstitutedandenantiomericallypure234trishydroxyalkylpyrrolidinesusinga13dipolarcycloadditionreactionaskeystep AT varelao synthesisofhighlysubstitutedandenantiomericallypure234trishydroxyalkylpyrrolidinesusinga13dipolarcycloadditionreactionaskeystep |
| _version_ |
1782029858820325376 |