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

09 March 2023, Version 2
This content is a preprint and has not undergone peer review at the time of posting.


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.


Diels-Alder cycloaddition
Asymmetric synthesis
chiral auxilary

Supplementary materials

Supporting Information for Enantioselective synthesis of a norbornene derivative
In this supporting information file, we report the proton and carbon 13 NMR spectra we had during our synthesis steps of each intermediate.


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