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Abstract:

Enantiomerically pure pyrrolidines have been obtained by 1,3-dipolar cycloaddition of stabilized azomethine ylides and sugar enones (dihydropyranones) derived from pentoses. Thus, the S-enone (menthyl 3,4-dideoxy-(1S)-pent-3-enopyranosid-2-ulose) was prepared from d-xylose, while the R analogue was obtained from l-arabinose. The dipoles were generated in situ from α-arylimino esters of common amino acids (glycine, alanine, or phenylalanine) and aromatic aldehydes (benzaldehyde, 3-formylpyridine and 4-methoxybenzaldehyde). Under optimized conditions, the cycloaddition reactions were highly diastereo- and regioselective to yield, in most of the cases, a very major adduct of the 16 theoretically possible. The diastereoselectivity relies on the strict stereocontrol exerted by the stereogenic center of the pyranone. Thus, the (S)-enone, derived from d-xylose, gave tetrasubstituted pyrrolidines having a defined stereochemistry for the four stereocenters of the ring, while they had the opposite configuration when starting from the (R)-dihydropyranone. Furthermore, some endo-cycloadducts underwent isomerization of the carbons vicinal to the nitrogen atom to afford pyrrolidines with a rather unusual stereochemistry for the direct dipolar cycloadditions. © 2014 American Chemical Society.

Registro:

Documento: Artículo
Título:Stereospecific synthesis of pyrrolidines with varied configurations via 1,3-dipolar cycloadditions to sugar-derived enones
Autor:Udry, G.A.O.; Repetto, E.; Varela, O.
Filiación:CIHIDECAR-CONICET-UBA, Departamento de Química Orgánica, Pabellón 2-Ciudad Universitaria, Buenos Aires 1428, Argentina
Palabras clave:Amino acids; Stereochemistry; Stereoselectivity; 1 ,3-dipolar cycloadditions; 1 ,3-Dipolarcycloaddition; Cycloaddition reaction; Diastereo-selectivity; Dipolar cycloadditions; Optimized conditions; Stereogenic centers; Stereospecific synthesis; Cycloaddition; 3 formylpyridine; alanine; aldehyde; anisaldehyde; arabinose; azomethine ylide; benzaldehyde; carbon; ester; glycine; ketone derivative; nitrogen; pentose; phenylalanine; pyran derivative; pyridine derivative; pyrrolidine derivative; sugar; unclassified drug; xylose; article; chemical structure; cycloaddition; dipole; isomerization; stereochemistry; stereospecificity; synthesis
Año:2014
Volumen:79
Número:11
Página de inicio:4992
Página de fin:5006
DOI: http://dx.doi.org/10.1021/jo500547y
Título revista:Journal of Organic Chemistry
Título revista abreviado:J. Org. Chem.
ISSN:00223263
CODEN:JOCEA
CAS:alanine, 56-41-7, 6898-94-8; anisaldehyde, 123-11-5, 50984-52-6; arabinose, 147-81-9; azomethine ylide, 107081-71-0, 1761-67-7, 176903-89-2; benzaldehyde, 100-52-7; carbon, 7440-44-0; glycine, 56-40-6, 6000-43-7, 6000-44-8; nitrogen, 7727-37-9; pentose, 53106-52-8; phenylalanine, 3617-44-5, 63-91-2; xylose, 25990-60-7, 58-86-6
Registro:https://bibliotecadigital.exactas.uba.ar/collection/paper/document/paper_00223263_v79_n11_p4992_Udry

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Citas:

---------- APA ----------
Udry, G.A.O., Repetto, E. & Varela, O. (2014) . Stereospecific synthesis of pyrrolidines with varied configurations via 1,3-dipolar cycloadditions to sugar-derived enones. Journal of Organic Chemistry, 79(11), 4992-5006.
http://dx.doi.org/10.1021/jo500547y
---------- CHICAGO ----------
Udry, G.A.O., Repetto, E., Varela, O. "Stereospecific synthesis of pyrrolidines with varied configurations via 1,3-dipolar cycloadditions to sugar-derived enones" . Journal of Organic Chemistry 79, no. 11 (2014) : 4992-5006.
http://dx.doi.org/10.1021/jo500547y
---------- MLA ----------
Udry, G.A.O., Repetto, E., Varela, O. "Stereospecific synthesis of pyrrolidines with varied configurations via 1,3-dipolar cycloadditions to sugar-derived enones" . Journal of Organic Chemistry, vol. 79, no. 11, 2014, pp. 4992-5006.
http://dx.doi.org/10.1021/jo500547y
---------- VANCOUVER ----------
Udry, G.A.O., Repetto, E., Varela, O. Stereospecific synthesis of pyrrolidines with varied configurations via 1,3-dipolar cycloadditions to sugar-derived enones. J. Org. Chem. 2014;79(11):4992-5006.
http://dx.doi.org/10.1021/jo500547y