As described in this paper, the Diels-Alder reaction of cyclopentadiene with a dienophile bearing a stereocontrolling element, known as chiral auxiliary (Oppolzer camphorsultam), provide endo-cycloadducts in good yields (74%) and high diastereofacial selectivity. The final functional group interconversion (FGI) step was not conducted due to a lack of time. However, if the latter was conducted, it would have been interesting to characterize our target hydroxy-product by measuring its optical rotatory power. This catalytic multi-step enantioselective synthesis was very interesting as it is an opportunity for undergraduate and engineering students to get familiarized with a total chiral synthesis and also with powerful characterization techniques. Analysis of our products by 1 H and 13 C NMR spectroscopy illustrates the importance of such a technique in the elucidation of a complex chemical structrue. Simultaneously, a proposed hypotheses are invoked as a possible explanation of the brown color origin of the imine intermediate (degradation or polymerization) which can be either confirmed or rejected by further analyses (e.g., DSC). Finally, even though the remarkable advances that have been made in the development of organometallic asymmetric catalysts, our synthesis could surely be carried out with organocatalysis (use of organic molecules as reaction catalysts) as reported in "The First Highly Enantioselective Organocatalytic Diels-Alder Reaction" research paper of David W. C. MacMillan, the 2021 Nobel Prize winner.