Catalytic Asymmetric Synthesis of Axially Chiral <i>o</i>-Iodoanilides by Phase-Transfer Catalyzed Alkylations

Catalytic asymmetric synthesis of axially chiral <i>o</i>-iodoacrylanilides and <i>N</i>-allyl-<i>o</i>-iodoanilides as useful chiral building blocks was achieved via chiral quaternary ammonium salt-catalyzed <i>N</i>-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