In Pursuit of β‐Amino‐α‐nitro‐β‐(trifluoromethyl) Ketones: Nitro‐Mannich versus Mannich‐Type Reactions

Abstract

The reactivity of α‐nitro ketones with trifluoromethyl aldimines has been studied for the first time. Whereas under nitro‐Mannich conditions only the facial stereoselectivity can be controlled, organocatalysed Mannich‐type reactions allowed complete control of the absolute and relative stereoselectivity, leading to highly functionalised β‐amino‐α‐nitro‐β‐(trifluoromethyl) compounds as diastereomerically pure compounds. The structures of the reactants play a key role in the geometrical and/or facial stereoselectivity.