Total Enantioselective Synthesis of a Norbornene Derivative via Lewis Acid Catalyzed Asymmetric Diels-Alder Reaction using the Oppolzer's Camphorsultam as a Chiral Auxilary

Abstract

In this paper, an efficient enantioselective synthesis of a norbornene derivative is described. Oppolzer's chiral sultam-directed asymmetric Diels-alder [4+2] cycloaddition was conducted as a crucial tool to control the diastereoselectivity of the cycloadduct leading to the desired enantioselective target molecule after the chiral auxilary removal. The synthesis process was demonstrated as a proof of study on a lab scale and the full experiment is addressed to advanced undergraduate students who are trained in organic synthesis and NMR spectroscopy.