Chemo-, regio-, and enantioselective synthesis of allylic nitrones via rhodium-catalyzed addition of oximes to allenes.

Abstract

The first chemo-, regio-, and enantioselective rhodium-catalyzed addition of oximes to allenes is reported. Using a Rh(i)/Josiphos catalyst system under mild conditions, the construction of allylic C-N bonds instead of C-O bonds was achieved. This method permits the atom-economic synthesis of branched allylic nitrones in good to quantitative yields with excellent enantioselectivities.