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...

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Detalles Bibliográficos
Publicado: 2017
Materias:
1,3-dipolar-cycloaddition
azomethine ylide
polyhydroxyalkylpyrrolidine
pyrrolidine
sugar enone
Acceso en línea:https://bibliotecadigital.exactas.uba.ar/collection/paper/document/paper_23656549_v2_n17_p4774_Udry
http://hdl.handle.net/20.500.12110/paper_23656549_v2_n17_p4774_Udry
Aporte de:
Biblioteca Digital - Facultad de Ciencias Exactas y Naturales (UBA) de Universidad de Buenos Aires
id paper:paper_23656549_v2_n17_p4774_Udry
record_format dspace
spelling paper:paper_23656549_v2_n17_p4774_Udry2023-06-08T16:35:50Z Synthesis of Highly Substituted and Enantiomerically Pure 2,3,4-Tris(hydroxyalkyl)pyrrolidines Using a 1,3-Dipolar Cycloaddition Reaction as Key Step 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 2017 https://bibliotecadigital.exactas.uba.ar/collection/paper/document/paper_23656549_v2_n17_p4774_Udry 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
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
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
publishDate 2017
url https://bibliotecadigital.exactas.uba.ar/collection/paper/document/paper_23656549_v2_n17_p4774_Udry
http://hdl.handle.net/20.500.12110/paper_23656549_v2_n17_p4774_Udry
_version_ 1768546276872290304

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