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 CHCl(3) to yield beta-lactams with high enantioselectivity (e.r. approximately 90:10) in solution. The extent of enantioselectivity was found to be dependent on the reaction temperature.
Ayitou
Anoklase Jean-Luc
AJ
Department of Chemistry and Molecular Biology, North Dakota State University, Fargo, North Dakota 58105, USA.
Jesuraj
Josepha L
JL
Barooah
Nilotpal
N
Ugrinov
Angel
A
Sivaguru
J
J