Fluorous chiral bis(oxazolines): Synthesis and application in asymmetric Henry reaction

A fluorous bis(oxazolines) was synthesized by a facile two-step process using malononitrile as the starting material. The compound was tested as a chiral ligand in copper-catalyzed Henry reactions of nitromethane with different aldehydes to afford the corresponding beta-nitroalcohols in 61-75% yield with enantioselectivities up to 99%. Furthermore, the fluorous ligand can be easily recovered and reused without significant loss in its activity. (C) 2013 Elsevier B.V. All rights reserved.