Chiral bispyridylamide metal complexes as catalysts for the enantioselective addition of TMSCN to aldehydes - INSA Toulouse - Institut National des Sciences Appliquées de Toulouse Access content directly
Journal Articles Journal of Organometallic Chemistry Year : 2004

Chiral bispyridylamide metal complexes as catalysts for the enantioselective addition of TMSCN to aldehydes

Oscar Belda
  • Function : Correspondent author
  • PersonId : 1078606

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Sophie Duquesne

Abstract

The use of (1R,2R)-N,N′-bis(2-pyridinecarboxyamido)-1,2-diphenylethane metal complexes as catalysts for the enantioselective addition of trimethylsilyl cyanide to aldehydes is described. Enantioselectivities up to 70% ee were obtained with a Ti(IV) catalyst. Complexes with Zr(IV), Sc(III), Yb(III) and Cu(II) afforded less selective catalysts. For the Zr(IV) complex, a rate and selectivity enhancement was observed when adding 0.5 equiv. of water with respect to the catalyst. Studies of the metal complexes involved in the reaction were carried out by means of 1H NMR spectroscopy. A Zr complex was shown by X-ray crystallography to exhibit distorted octahedral coordination, with the four nitrogen atoms of the doubly deprotonated ligand essentially in one plane.

Dates and versions

hal-02957819 , version 1 (05-10-2020)

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Oscar Belda, Sophie Duquesne, Andreas Fischer, Christina Moberg. Chiral bispyridylamide metal complexes as catalysts for the enantioselective addition of TMSCN to aldehydes. Journal of Organometallic Chemistry, 2004, 689 (23), pp.3750-3755. ⟨10.1016/j.jorganchem.2004.06.014⟩. ⟨hal-02957819⟩

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