Synthesis 2005(20): 3620-3626  
DOI: 10.1055/s-2005-916038
PAPER
© Georg Thieme Verlag Stuttgart · New York

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;
Further Information

Publication History

Received 26 May 2005
Publication Date:
12 October 2005 (eFirst)

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.

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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: +44(1223)336033, e-mail: deposit@ccdc.cam.ac.uk].