Synthesis of Allylic Amines by Asymmetric Transfer Hydrogenation of α,β-Unsaturated N-(tert-Butylsulfinyl)imines
| Autor: | David Guijarro, Yeshua Sempere, Débora Ruiz-Martínez, Elisabet Selva, Óscar Pablo |
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| Přispěvatelé: | Universidad de Alicante. Departamento de Química Orgánica, Universidad de Alicante. Instituto Universitario de Síntesis Orgánica, Catálisis Estereoselectiva en Síntesis Orgánica (CESO), Síntesis Asimétrica (SINTAS), Grupo de Fotoquímica y Electroquímica de Semiconductores (GFES) |
| Rok vydání: | 2017 |
| Předmět: |
Allylic rearrangement
Ruthenium catalyst Carbon atom 010405 organic chemistry Chemistry Organic Chemistry Absolute configuration ATH Isopropyl alcohol 010402 general chemistry Transfer hydrogenation 01 natural sciences Medicinal chemistry 0104 chemical sciences Asymmetric transfer hydrogenation chemistry.chemical_compound Química Orgánica Allylic amine Organic chemistry Amine gas treating Chemoselectivity Enantiomer N-sulfinylimine |
| Zdroj: | RUA. Repositorio Institucional de la Universidad de Alicante Universidad de Alicante (UA) |
| ISSN: | 1520-6904 0022-3263 |
| DOI: | 10.1021/acs.joc.7b02472 |
| Popis: | 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. 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). |
| Databáze: | OpenAIRE |
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