(S)-Binam-L-prolinamide as organocatalyst for the enantioselective conjugate addition of α-alkoxyketones to β-nitrostyrene derivatives

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Title: (S)-Binam-L-prolinamide as organocatalyst for the enantioselective conjugate addition of α-alkoxyketones to β-nitrostyrene derivatives
Authors: Guillena, Gabriela | Nájera, Carmen | Viózquez Cámara, Santiago Fidel | Yus, Miguel
Research Group/s: Derivados de Aminoácidos y Péptidos en Síntesis Orgánica | Procesos Catalíticos en Síntesis Orgánica | Nuevas Metodologías en Síntesis Orgánica
Center, Department or Service: Universidad de Alicante. Departamento de Química Orgánica
Keywords: Asymmetric synthesis | Conjugate addition | Nitroolefins | Organocatalysis | Prolinamides
Knowledge Area: Química Orgánica
Issue Date: 4-Feb-2011
Publisher: Arkat USA, Inc.
Citation: GUILLENA TOWNLEY, Gabriela, et al. "(S)-Binam-L-prolinamide as organocatalyst for the enantioselective conjugate addition of α-alkoxyketones to β-nitrostyrene derivatives". ARKIVOC. Vol. 2011 (III). ISSN 1551-7004, pp. 166-178
Abstract: (S)-Binam-L-prolinamide (20 mol%) catalyze the enantioselective Michael addition of several α-alkoxyketones to different β-nitrostyrene derivatives. In the study of the optimization of the reaction conditions it was found surprisingly that hexane is the solvent of choice to carry out such transformation. Under these reaction conditions, the corresponding highly functionalized products were obtained in good yields (up to 90%), mainly as syn-diastereomers with moderate diastereo- and enantioselectivities.
Sponsor: This research was supported by the Ministerio de Ciencia e Innovación (Projects CTQ2007-62771/BQU, CTQ2007-65218/BQU and Consolider Ingenio 2010 CSD2007-00006), the Generalitat Valenciana (Project PROMETEO/2009/039, FEDER) and the University of Alicante (UA).
URI: http://hdl.handle.net/10045/16189
ISSN: 1551-7004 (Print) | 1551-7012 (Online)
Language: eng
Type: info:eu-repo/semantics/article
Peer Review: si
Publisher version: http://www.arkat-usa.org/arkivoc-journal/browse-arkivoc/2011/3/
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