8-Amino-5,6,7,8-tetrahydroquinolines as ligands in iridium(III) catalysts for the reduction of aryl ketones by asymmetric transfer hydrogenation (ATH)
| Autor: | Marco Fusè, Daniele Zerla, Isabella Rimoldi, Raffaella Gandolfi, Giorgio Facchetti, Carlo Castellano, Edoardo Cesarotti, Michela M. Pellizzoni |
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| Přispěvatelé: | Zerla, Daniele, Facchetti, Giorgio, Fuse', Marco, Pellizzoni, Michela, Castellano, Carlo, Cesarotti, Edoardo, Gandolfi, Raffaella, Rimoldi, Isabella |
| Jazyk: | angličtina |
| Rok vydání: | 2014 |
| Předmět: |
Trifluoromethyl
Aryl water Organic Chemistry Diastereomer chemistry.chemical_element Enantioselective transfer hydrogenation Transfer hydrogenation Catalysis Reaction rate Inorganic Chemistry chemistry.chemical_compound Physical and Theoretical Chemistry chemistry Organic chemistry alcohol-dehydrogenase Stereoselectivity Iridium |
| Zdroj: | Università degli Studi di Milano-IRIS |
| Popis: | Aqua iridium(III) complexes with 8-amino-5,6,7,8-tetrahydroquinolines CAMPY L1 and its derivatives as chiral ligands proved to be very efficient catalysts for the reduction of a wide range of prochiral aryl ketones, revealing a variety of behaviours in terms of reaction rate and stereoselectivity. As standard substrates, differently substituted acetophenones were studied and good enantioselectivity (86% ee) was achieved in the reduction of 1-(o-tolyl)ethan-1-one 6. Particularly interesting was the ATH reaction in the case of β-amino keto esters, precursors of β-lactams and azetidinones. The best results were obtained with [Cp*Ir(H2O)(L1)]SO4affording the corresponding diastereomeric alcohols in an (R,S)-configuration with an excellent 99% ee in the reduction of 2-(benzamido methyl)-3-oxo-3-(4-(trifluoromethyl)phenyl)propanoate 12. © 2014 Elsevier Ltd. All rights reserved. |
| Databáze: | OpenAIRE |
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