Journal of the American Chemical Society, Vol.131, No.32, 11314-11314, 2009
Enantiospecific Photochemical Norrish/Yang Type II Reaction of Nonbiaryl Atropchiral alpha-Oxoamides in Solution-Axial to Point Chirality Transfer
alpha-Oxoamides 1 with o-tert-butyl substitution on the N-phenyl moiety were found to be stable axially chiral atropisomers. These axially chiral alpha-oxoamides undergo enantiospecific photochemical gamma-Hydrogen abstraction in CHCl3 to yield beta-lactams with high enantioselectivity (e.r. similar to 90:10) in solution. The extent of enantioselectivity was found to be dependent on the reaction temperature.