Abstract:
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
Registro:
Documento: |
Artículo
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Título: | Synthesis of Highly Substituted and Enantiomerically Pure 2,3,4-Tris(hydroxyalkyl)pyrrolidines Using a 1,3-Dipolar Cycloaddition Reaction as Key Step |
Autor: | Udry, G.A.O.; Repetto, E.; Vega, D.R.; Varela, O. |
Filiación: | Universidad de Buenos Aires., Facultad de Ciencias Exactas y Naturales. Departamento de Química Orgánica., Pabellón 2, Ciudad Universitaria, Buenos Aires, C1428EHA, Argentina Consejo Nacional de Investigaciones Científicas y Técnicas (CONICET)-UBA., Centro de Investigación en Hidratos de Carbono (CIHIDECAR)., Buenos Aires, Argentina Departamento Física de la Materia Condensada, GAIyANN-CAC-CNEA and ECyT-UNSAM, Av. Gral. Paz 1499–1650. San Martín, Buenos Aires, Argentina
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Palabras clave: | 1,3-dipolar-cycloaddition; azomethine ylide; polyhydroxyalkylpyrrolidine; pyrrolidine; sugar enone |
Año: | 2017
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Volumen: | 2
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Número: | 17
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Página de inicio: | 4774
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Página de fin: | 4778
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DOI: |
http://dx.doi.org/10.1002/slct.201701068 |
Título revista: | ChemistrySelect
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Título revista abreviado: | ChemistrySelect
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ISSN: | 23656549
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Registro: | https://bibliotecadigital.exactas.uba.ar/collection/paper/document/paper_23656549_v2_n17_p4774_Udry |
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Citas:
---------- APA ----------
Udry, G.A.O., Repetto, E., Vega, D.R. & Varela, O.
(2017)
. Synthesis of Highly Substituted and Enantiomerically Pure 2,3,4-Tris(hydroxyalkyl)pyrrolidines Using a 1,3-Dipolar Cycloaddition Reaction as Key Step. ChemistrySelect, 2(17), 4774-4778.
http://dx.doi.org/10.1002/slct.201701068---------- CHICAGO ----------
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"
. ChemistrySelect 2, no. 17
(2017) : 4774-4778.
http://dx.doi.org/10.1002/slct.201701068---------- MLA ----------
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"
. ChemistrySelect, vol. 2, no. 17, 2017, pp. 4774-4778.
http://dx.doi.org/10.1002/slct.201701068---------- VANCOUVER ----------
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. ChemistrySelect. 2017;2(17):4774-4778.
http://dx.doi.org/10.1002/slct.201701068