Dual chiral silver catalyst in the synthetic approach to the core of hepatitis C virus inhibitor GSK 625433 using enantioselective 1,3-dipolar cycloaddition of azomethine ylides and electrophilic alkenes

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Title: Dual chiral silver catalyst in the synthetic approach to the core of hepatitis C virus inhibitor GSK 625433 using enantioselective 1,3-dipolar cycloaddition of azomethine ylides and electrophilic alkenes
Authors: Chabour, Ihssene | Castelló Moncayo, Luis Miguel | Mancebo Aracil, Juan | Martín Rodríguez, María | Retamosa Hernández, María de Gracia | Nájera, Carmen | Sansano, Jose M.
Research Group/s: Síntesis Asimétrica (SINTAS)
Center, Department or Service: Universidad de Alicante. Departamento de Química Orgánica | Universidad de Alicante. Instituto Universitario de Síntesis Orgánica
Keywords: Dual chiral silver | Catalysts | 1,3-dipolar cycloaddition | Azomethine ylides | Electrophilic alkenes
Knowledge Area: Química Orgánica
Issue Date: 15-Oct-2017
Publisher: Elsevier
Citation: Tetrahedron: Asymmetry. 2017, 28(10): 1423-1429. doi:10.1016/j.tetasy.2017.08.011
Abstract: The asymmetric 1,3-dipolar cycloaddition of an imino ester 5 with tert-butyl acrylate is catalyzed by a dual chiral silver(I) complex formed from a chiral phosphoramidite 14 and the chiral silver(I) binolphosphate (R)-17. This reaction is selected to achieve the synthesis of enantiomerically enriched key structures to access the third generation of GSK HCV inhibitors. The scope of this dual chiral catalytic system is analyzed by employing different imino esters and dipolarophiles, and also compared with the same cycloaddition reactions performed with the chiral phosphoramidite 14·AgClO4 complex.
Sponsor: Financial support was provided by the Spanish Ministerio de Ciencia e Innovación (MICINN) (projects CTQ2010-20387, and Consolider Ingenio 2010, CSD2007-00006), the Spanish Ministerio de Economía y Competitividad (MINECO) (projects CTQ2013-43446-P and CTQ2014-51912-REDC), the Spanish Ministerio de Economía, Industria y Competitividad, Agencia Estatal de Investigación (AEI) and Fondo Europeo de Desarrollo Regional (FEDER, EU) (projects CTQ2016-76782-P and CTQ2016-81797-REDC), the Generalitat Valenciana (PROMETEO 2009/039 and PROMETEOII/2014/017), and the University of Alicante.
URI: http://hdl.handle.net/10045/71011
ISSN: 0957-4166 (Print) | 1362-511X (Online)
DOI: 10.1016/j.tetasy.2017.08.011
Language: eng
Type: info:eu-repo/semantics/article
Rights: © 2017 Elsevier Ltd.
Peer Review: si
Publisher version: http://dx.doi.org/10.1016/j.tetasy.2017.08.011
Appears in Collections:INV - SINTAS - Artículos de Revistas

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