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

Abstract

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.

GRAPHICAL ABSTRACT

Keywords:

• BINOL
• cinchona alkaloids
• inversion
• Mitsunobu reaction
• multistereogenic chirality
• retention

ACKNOWLEDGMENTS

X. L. W. thanks F. E. Zhu and K. Z. Jiang (HZNU) for their help, and also C. G. Xia (Lanzhou Institute of Chemical Physics, Chinese Academy of Sciences) and Y. Lu (National University of Singapore) for their helpful discussions.

Notes

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