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)]SO 4 affording 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.
8-Amino-5,6,7,8-tetrahydroquinolines as ligands in iridium(III) catalysts for the reduction of aryl ketones by asymmetric transfer hydrogenation (ATH) / D. Zerla, G. Facchetti, M. Fusè, M. Pellizzoni, C. Castellano, E. Cesarotti, R. Gandolfi, I. Rimoldi. - In: TETRAHEDRON-ASYMMETRY. - ISSN 0957-4166. - 25:13-14(2014), pp. 1031-1037.
|Titolo:||8-Amino-5,6,7,8-tetrahydroquinolines as ligands in iridium(III) catalysts for the reduction of aryl ketones by asymmetric transfer hydrogenation (ATH)|
ZERLA, DANIELE SERGIO (Primo)
FACCHETTI, GIORGIO (Secondo)
GANDOLFI, RAFFAELLA (Penultimo)
RIMOLDI, ISABELLA (Corresponding)
|Parole Chiave:||Enantioselective transfer hydrogenation; alcohol-dehydrogenase; water|
|Settore Scientifico Disciplinare:||Settore CHIM/03 - Chimica Generale e Inorganica|
Settore CHIM/11 - Chimica e Biotecnologia delle Fermentazioni
|Data di pubblicazione:||2014|
|Digital Object Identifier (DOI):||http://dx.doi.org/10.1016/j.tetasy.2014.06.003|
|Appare nelle tipologie:||01 - Articolo su periodico|
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