Enantioselective synthesis of polysubstituted prolines by Binap-silver-catalyzed 1,3-dipolar cycloadditions

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Title: Enantioselective synthesis of polysubstituted prolines by Binap-silver-catalyzed 1,3-dipolar cycloadditions
Authors: Nájera, Carmen | Retamosa Hernández, María de Gracia | Sansano, Jose M. | Cózar Ruano, Abel de | Cossío Mora, Fernando Pedro
Research Group/s: Procesos Catalíticos en Síntesis Orgánica
Center, Department or Service: Universidad de Alicante. Departamento de Química Orgánica | Universidad de Castilla-La Mancha. Área de Química Orgánica | Universidad del País Vasco. Departamento de Química Orgánica I
Keywords: Enantioselective | 1,3-dipolar cycloaddition | Proline
Knowledge Area: Química Orgánica
Date Created: 24-Oct-2008
Issue Date: 12-Dec-2008
Publisher: Elsevier
Citation: NÁJERA DOMINGO, Carmen, et al. "Enantioselective synthesis of polysubstituted prolines by Binap-silver-catalyzed 1,3-dipolar cycloadditions". Tetrahedron: Asymmetry. Vol. 19, Issue 24 (12 Dec. 2008). ISSN 0957-4166, pp. 2913-2923
Abstract: The enantioselective 1,3-dipolar cycloaddition reaction of stabilized azomethine ylides, generated from iminoesters, with maleimides was efficiently achieved by intermediacy of an equimolar mixture of chiral (R)- or (S)-Binap and AgClO4. The high stability of the titled catalytic metal-complex to light exposure and its insolubility in toluene made possible its recovery and reutilization in other new process. In order to get a better understanding of the behavior of these chiral catalysts, we have carried out DFT1 calculations demonstrating the experimentally observed high enantio- and endo-selectivity through a very asynchronous transition state.
Sponsor: This work has been supported by the DGES of the Spanish Ministerio de Educación y Ciencia (MEC) (Consolider INGENIO 2010 CSD2007-00006, CTQ2007-62771/BQU, and CTQ2004-00808/BQU), Generalitat Valenciana (CTIOIB/2002/320, GRUPOS03/134 and GV05/144), and by the University of Alicante. M.G. Retamosa thanks the University of Alicante for a predoctoral fellowship.
URI: http://hdl.handle.net/10045/9729
ISSN: 0957-4166
DOI: 10.1016/j.tetasy.2008.12.021
Language: eng
Type: info:eu-repo/semantics/article
Peer Review: si
Publisher version: http://dx.doi.org/10.1016/j.tetasy.2008.12.021
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