Synthesis of Allylic Amines by Asymmetric Transfer Hydrogenation of α,β-Unsaturated N-(tert-Butylsulfinyl)imines

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Title: Synthesis of Allylic Amines by Asymmetric Transfer Hydrogenation of α,β-Unsaturated N-(tert-Butylsulfinyl)imines
Authors: Selva, Elisabet | Sempere, Yeshua | Ruiz Martínez, Débora | Pablo, Óscar | Guijarro, David
Research Group/s: Catálisis Estereoselectiva en Síntesis Orgánica (CESO) | Síntesis Asimétrica (SINTAS) | Grupo de Fotoquímica y Electroquímica de Semiconductores (GFES)
Center, Department or Service: Universidad de Alicante. Departamento de Química Orgánica | Universidad de Alicante. Instituto Universitario de Síntesis Orgánica
Keywords: Allylic amine | Asymmetric transfer hydrogenation | ATH | N-sulfinylimine | Ruthenium catalyst | Isopropyl alcohol
Knowledge Area: Química Orgánica
Issue Date: 17-Nov-2017
Publisher: American Chemical Society
Citation: Journal of Organic Chemistry. 2017, 82(24): 13693-13699. doi:10.1021/acs.joc.7b02472
Abstract: Primary allylic amines with enantiomeric excesses from 97 to >99% were prepared by asymmetric transfer hydrogenation of α,β-unsaturated N-(tert-butylsulfinyl)ketimines followed by removal of the sulfinyl group. The effect caused by different substituents at the C═C bond and at the iminic carbon atom on the chemoselectivity of the reduction was studied. The desired enantiomer of the final allylic amine can be synthesized by choosing the sulfinyl group with the appropriate absolute configuration.
Sponsor: This work was generously supported by the Spanish Ministerio de Ciencia e Innovación (MICINN; Grant CTQ2011-24151), the Spanish Ministerio de Economía, Industria y Competitividad (Grant CTQ2015-66624-P), and the University of Alicante. E.S. thanks the University of Alicante for a predoctoral fellowship. O.P. thanks the Spanish Ministerio de Educación for a predoctoral fellowship (Grant AP-2008-00989).
ISSN: 0022-3263 (Print) | 1520-6904 (Online)
DOI: 10.1021/acs.joc.7b02472
Language: eng
Type: info:eu-repo/semantics/article
Rights: © 2017 American Chemical Society
Peer Review: si
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Appears in Collections:INV - SINTAS - Artículos de Revistas
INV - GFES - Artículos de Revistas
INV - CESO - Artículos de Revistas

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