An asymmetric base-catalyzed Diels-Alder reaction of 3-hydroxy-2-pyrone with N-methylmaleimide was achieved by using cinchona alkaloids as asymmetric catalysts. The reaction catalyzed by cinchonidine afforded endo-adduct in 77% ee, and opposite enantiomer of 71% ee was obtained with cinchonine.
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Okamura et al. (1996) studied this question.
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