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Donor–acceptor cyclopropanes were engaged in a [3+3]-annulation reaction with γ-hydroxyenones. Sc(OTf)3 was found to be the best catalyst, and 2,4,4,5-tetrasubstituted tetrahydropyran products were obtained in good yields under mild reaction… Click to show full abstract
Donor–acceptor cyclopropanes were engaged in a [3+3]-annulation reaction with γ-hydroxyenones. Sc(OTf)3 was found to be the best catalyst, and 2,4,4,5-tetrasubstituted tetrahydropyran products were obtained in good yields under mild reaction conditions. The generality of the reaction permitted the synthesis of tetrasubstituted tetrahydropyrans bearing aryl, alkyl, and heteroaromatic groups. A catalytic asymmetric variant of this process was also studied preliminary with a chiral PyBOX ligand.
Journal Title: European Journal of Organic Chemistry
Year Published: 2017
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