N-Heterocyclic Carbene-Catalyzed Atroposelective Synthesis of N-N Axially Chiral 3-Amino Quinazolinones

Although the atroposelective synthesisof biaryls and related compoundsbearing axially chiral C-C bonds is well-known, the synthesisof axially chiral C-N bond-containing compounds is relativelyless explored, and the construction of axially chiral N-N bondshas received only scant attention. Demonstrated herein is the N-heterocycliccarbene (NHC)-catalyzed selective amidation reaction, leading to theatroposelective synthesis of N-N axially chiral 3-amino quinazolinones.The NHC-catalyzed reaction of quinazolinones containing a free N-Hmoiety with & alpha;,& beta;-unsaturated aldehydes under oxidativeconditions furnished the atropisomeric quinazolinone derivatives undermild conditions and broad scope. Preliminary studies on experimentaland density functional theory-based N-N rotational barrierdetermination are also presented.