The stereoselectivity of a Diels-Alder reaction within the periphery of hierarchically assembled titanium(IV) helicates formed from mixtures of achiral, reactive and chiral, unreactive ligands is investigated in detail. Following the pathway of the chiral induction, the chiral ligands, solvents as well as substituents at the dienophile are carefully varied. Based on the results of the stoichiometric reaction a secondary amine catalyzed nitro-Michael reaction is performed as well which affords reasonable diastereoselectivities.
Keywords: hierarchical helicates; remote-control; stereoselectivity; Diels-Alder reaction; enamine catalysis
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Van Craen, D.; Begall, J.; Grosskurth, J.; Himmel, L.; Linnenberg, O.; Isaak, E.; Albrecht, M. Beilstein Arch. 2020, 202082. doi:10.3762/bxiv.2020.82.v1
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