Diels–Alder reaction of (3R, 5S)-5-benzoyloxy-2,2,6,6-tetramethyl-3-heptyl acrylate (TMHD-acrylate)1 with cyclopentadiene in the presence of TiCl4·(ArnHg)m complexed Lewis acids gives (1R,4R,6R)-2-norbornene-6-carboxylate derivative 4 predominantly, whereas the reaction in the presence of TiCl4 alone affords its enantiomer 2 preferentially.
I. Kadota, K. Kobayashi, N. Asao and Y. Yamamoto, J. Chem. Soc., Chem. Commun., 1995, 1271 DOI: 10.1039/C39950001271
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