Abstract
TiCl4 and ZnCl2 supported on silica gel catalyze the reactions of furan with methyl, (1R,2S,5R)-menthyl, and (1R,2S,5R)-8-phenylmenthyl acrylates. The best results are obtained when reactions are carried out without a solvent. The endo/exo and diastereofacial selectivities depend on the nature of the catalyst and on the reaction conditions. With the (1R,2S,5R)-menthyl acrylate 44% de in endo cycloadducts and 20% de in exo cycloadducts are the best asymmetric inductions. With the (1R,2S,5R)-8-phenylmenthyl acrylate 68% de in endo and 70% de in exo cycloadducts are obtained.
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