Enantioselective Amination of Silyl Enol Ethers

Significance

Chiral α-aminoketones are most often used in their reduced form as syn- or antiα-amino alcohols. A number of procedures have been developed to access such amino alcohols (or their precursors), but the above method complements the previous ones and provides an experimentally simple protocol. The one-pot sequence (7 to 4a) circumventing the potentially sensitive handling of silyl enol ethers 1 is particularly attractive. The Rh(II) catalyst 3 catalyzes both reactions efficiently by sequential addition of a hydride, then the iodoimine.