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

<div><p></p><p>An efficient approach toward the construction of multistereogenic binaphthol (BINOL)–derived alkaloids with C₂-axial and sp³ central chirality has been accomplished. 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.</p>