The reactivity of alfa-nitro ketones with trifluoromethyl aldimines is studied for the first time. While under nitro-Mannich conditions only the facial stereoselectivity can be controlled, organocatalysed Mannich-type reactions allowed a complete control of absolute and relative stereoselectivity, leading to highly functionalised β-amino alfa-nitro β-trifluoromethyl compounds as diastereomerically pure compounds. A key role on the geometrical and/or facial stereoselectivity is played by the structure of reactants.
In pursuit of β-amino α-nitro β-trifluoromethyl ketones: nitro-Mannich vs Mannich-type reactions / Fioravanti, Stefania; Pelagalli, Alessia; Pellacani, Lucio. - In: EUROPEAN JOURNAL OF ORGANIC CHEMISTRY. - ISSN 1099-0690. - STAMPA. - 23(2017), pp. 3373-3380. [10.1002/ejoc.201700510]
In pursuit of β-amino α-nitro β-trifluoromethyl ketones: nitro-Mannich vs Mannich-type reactions
FIORAVANTI, Stefania
;PELAGALLI, ALESSIA;PELLACANI, Lucio
2017
Abstract
The reactivity of alfa-nitro ketones with trifluoromethyl aldimines is studied for the first time. While under nitro-Mannich conditions only the facial stereoselectivity can be controlled, organocatalysed Mannich-type reactions allowed a complete control of absolute and relative stereoselectivity, leading to highly functionalised β-amino alfa-nitro β-trifluoromethyl compounds as diastereomerically pure compounds. A key role on the geometrical and/or facial stereoselectivity is played by the structure of reactants.| File | Dimensione | Formato | |
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