Catalytic asymmetric synthesis of axially chiral o-iodoanilides by phase-transfer catalyzed alkylations.

Catalytic asymmetric synthesis of axially chiral o-iodoacrylanilides and N-allyl-o-iodoanilides as useful chiral building blocks was achieved via chiral quaternary ammonium salt-catalyzed N-alkylations under phase-transfer conditions. The transition-state structure for the present reaction is discussed on the basis of the X-ray crystal structure of ammonium anilide.