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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 (2019). Synthesis and crystal structures of chiral ferrocene and ruthenocene substituted aminomethylnaphthols obtained through Betti-condensation. Polyhedron, 165:177-187.

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% ee.

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% ee.

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Item Type:Journal Article, refereed, original work
Communities & Collections:07 Faculty of Science > Department of Chemistry
Dewey Decimal Classification:540 Chemistry
Scopus Subject Areas:Physical Sciences > Physical and Theoretical Chemistry
Physical Sciences > Inorganic Chemistry
Physical Sciences > Materials Chemistry
Uncontrolled Keywords:Chiral metallocenes Absolute configuration Crystal structures Chiral ligands Diethyl zinc
Language:English
Date:1 June 2019
Deposited On:09 Apr 2019 12:33
Last Modified:01 Jun 2021 00:03
Publisher:Elsevier
ISSN:0277-5387
OA Status:Green
Publisher DOI:https://doi.org/10.1016/j.poly.2019.03.019
Project Information:
  • : FunderNational Science Fund, Bulgaria
  • : Grant IDUNA 17/2005
  • : Project Title
  • : FunderNational Science Fund, Bulgaria
  • : Grant IDDRNF-02/13/2009
  • : Project Title

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