Synthesis and crystal structures of chiral ferrocene and ruthenocene substituted aminomethylnaphthols obtained through Betti-condensation

Dikova, Krasimira; Kostova, Kalina; Simova, Svetlana; Linden, Anthony; Chimov, Angel; Dimitrov, Vladimir

doi:10.5167/uzh-170250

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Dikova, K., Kostova, K., Simova, S., Linden, A., Chimov, A., & Dimitrov, V. (2019). Synthesis and crystal structures of chiral ferrocene and ruthenocene substituted aminomethylnaphthols obtained through Betti-condensation. Polyhedron, 165, 177–187. https://doi.org/10.1016/j.poly.2019.03.019

Abstract

Ferrocene- and ruthenocenecarboxaldehydes have been employed in Betti-type condensation reactions with 2-naphthol and (S)-phenylethylamine to give metallocenyl-substituted aminomethylnaphthols in a diastereoisomerically pure form. The absolute configurations of the new chiral compounds have been determined by means of NMR experiments and confirmed by X-ray crystallography. The chiral metallocenyl-aminomethylnaphthols have been tested as pre-catalysts for the addition of diethyl zinc to aldehydes, with enantioselectivities of up to 88%