Highly Stereoselective Synthesis of Cyclopropanes Based on the Ferrocenoyl Nitrogen Ylide

Ling Shi; Peng Wang; Xueyuan Liu; Weimin Liu; Yongmin Liang

doi:10.1055/s-2004-831176

PAPER

Highly Stereoselective Synthesis of Cyclopropanes Based on the Ferrocenoyl Nitrogen Ylide

Ling Shi^a, Peng Wang^a, Xueyuan Liu^a, Weimin Liu^b, Yongmin Liang*^a,b
^a Department of Chemistry and State Key Laboratory of Applied Organic Chemistry, Lanzhou University, Lanzhou 730000, P. R. China
^b State Key Laboratory of Solid Lubrication, Lanzhou Institute of Chemical Physics, Chinese Academy of Sciences, Lanzhou 730000, P. R. China
Fax: +86(931)8912582; e-Mail: liangym1@hotmail.com;

Abstract

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Abstract

Ferrocenoyl cyclopropane derivatives were prepared via the reaction of an electron-deficient olefin and a first prepared ferrocenoyl nitrogen ylide. The new compounds 2a-11a have been given in good yields and high stereoselectivity (the ratios of trans to cis diastereoisomers were above 99:1) under the optimum condition and characterized by ¹H NMR, ¹³C NMR, FAB-MS and IR. The X-ray crystal structure of 8a has also been determined.

Key words

cyclopropanation - ferrocenoyl nitrogen ylide - stereoselective synthesis - electron-deficient - structure

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References

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Crystallographic data for the structural analysis has been deposited with the Cambridge Crystallographic Data Centre, CCDC No. 228258 for compound 8a. Copies of this information may be obtained free of charge from: The Director, CCDC, 12 Union Road, Cambridge, CB2 1EZ, UK, Fax: +44(1223)336033; email: deposit@ccdc.cam.ac.uk or www: http://www.ccdc.cam.ac.uk.