Investigation of the Mitsunobu Reaction of BINOL and Cinchona Alkaloids: Inversion or Retention of Configuration?

The reaction of BINOL and cinchona alkaloids was occurred smoothly under the Mitsunobu conditions, which led to the synthesis of a new family of complicated functional molecules based on chiral BINOL and cinchona alkaloids. In addition, on the basis of the experimental results, we provided a possible explanation for the intramolecular tertiary amine-induced retention of configuration at C9 of cinchona alkaloids while the inversion of configuration was observed with general alcohols under classic Mitsunobu conditions.