Novel C2-Symmetric 1,1′-Disubstituted Ferrocenyl Aziridino Alcohol Ligands: Remarkable Improvement of Enantioselectivity in the Catalytic Asymmetric Addition of Diethylzinc to Aldehydes

Min-Can Wang; Xue-Hui Hou; Cui-Lian Xu; Lan-Tao Liu; Gui-Lan Li; De-Kun Wang

doi:10.1055/s-2005-916038

PAPER

Novel C ₂-Symmetric 1,1′-Disubstituted Ferrocenyl Aziridino Alcohol Ligands: Remarkable Improvement of Enantioselectivity in the Catalytic Asymmetric Addition of Diethylzinc to Aldehydes

Min-Can Wang*, Xue-Hui Hou, Cui-Lian Xu, Lan-Tao Liu, Gui-Lan Li, De-Kun Wang
Department of Chemistry, Zhengzhou University, Zhengzhou, Henan 450052, P. R. of China
Fax: +86(371)67769024; e-Mail: wangmincan@zzu.edu.cn;

Abstract

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Abstract

A series of novel chiral C ₂-symmetric 1,1′-disubstituted ferrocenyl aziridino alcohols have been readily synthesized and applied as catalysts to promote enantioselective addition of diethylzinc to aldehydes affording the corresponding 1-propanols in up to 99.5% enantiomeric excess with excellent yields. The effect of the ligand structure on the enantioselectivity was examined. The results showed that the C ₂-symmetric ferrocenyl β-amino alcohol ligands could produce an excellent asymmetric environment for the asymmetric addition of diethylzinc to aldehydes. The absolute configuration of chiral C ₂-symmetric ferrocenyl aziridino alcohol ligand 8j was confirmed by X-ray diffraction analysis.

Key words

aziridino alcohols - ferrocenyl - asymmetric addition - diethylzinc - aldehydes

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References

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Novel C 2-Symmetric 1,1′-Disubstituted Ferrocenyl Aziridino Alcohol Ligands: Remarkable Improvement of Enantioselectivity in the Catalytic Asymmetric Addition of Diethylzinc to Aldehydes

Novel C ₂-Symmetric 1,1′-Disubstituted Ferrocenyl Aziridino Alcohol Ligands: Remarkable Improvement of Enantioselectivity in the Catalytic Asymmetric Addition of Diethylzinc to Aldehydes