On the use of phosphoramidite ligands in copper-catalyzed asymmetric transformations with trialkylaluminum reagents.
[reaction: see text] Phosphoramidites based on BINOL readily react with trimethylaluminum in "noncoordinating" solvents, leading to the corresponding aminophosphine which is the real ligand in copper-catalyzed asymmetric transformations. This artifact explains the experimental differences in the asymmetric ring opening of meso bicyclic hydrazines using dialkylzinc or trialkylaluminum reagents as nucleophiles.
Bournaud
Chloée
C
Laboratoire de Chimie Thérapeutique, UMR 8638 associée au CNRS et à l'Université René Descartes, Faculté des Sciences Pharmaceutiques et Biologiques, 4 av de l'Observatoire, 75270 Paris Cedex 06, France.
Falciola
Caroline
C
Lecourt
Thomas
T
Rosset
Stéphane
S
Alexakis
Alexandre
A
Micouin
Laurent
L