Frozen chirality: Achiral naphthamide 1 can be crystallized to give chiral 1*, whose chiral molecular conformation is retained (“frozen”) after the crystals are dissolved in cold THF. Asymmetric photocycloaddition of 1* with 9-cyanoanthracene (9-CNAN) in solution gives cycloadduct 2 with high enantioselectivity.
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Sakamoto et al. (2005) studied this question.
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