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

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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10

Crystallographic data for the structure reported in this paper have been deposited with the Cambridge Crystallographic Data Centre as supplementary publication no. CCDC-272339. Copies of the data can be obtained free of charge on application to CCDC, 12 Union Road, CAMBRIDGE, CB2 1EZ, UK [fax: [phone], e-mail: [e-mail]].