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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
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
Palabras clave:1,3-dipolar-cycloaddition; azomethine ylide; polyhydroxyalkylpyrrolidine; pyrrolidine; sugar enone
Año:2017
Volumen:2
Número:17
Página de inicio:4774
Página de fin:4778
DOI: http://dx.doi.org/10.1002/slct.201701068
Título revista:ChemistrySelect
Título revista abreviado:ChemistrySelect
ISSN:23656549
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