281. A. Quintard, A. Alexakis,
     “Highly Enantioselective One-Pot Copper-Catalyzed 1,4 Addition/Organocatalyzed α-Substitution of Enals”
     Adv. Synth. Catal. 2010, 352, 1856-1860.

The asymmetric copper-catalyzed addition of dialkylzinc to enals followed by organocatalyzed one-pot aldehyde α-functionalization has been accomplished providing CC, CCl or CF bond formation. These simple procedures led to the creation of two contiguous stereocenters in excellent enantioselectivities (typical ee=99%). This methodology has been applied in the synthesis of (2S,3S) isomer of Valnoctamide®.

DOI : 10.1002/adsc.201000309 

archive ouverte unige:11964