Highly Stereoselective Synthesis of Cyclopropanes Based on the Ferrocenoyl Nitrogen Ylide

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

References

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18

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: [phone]; email: [e-mail] or www: http://www.ccdc.cam.ac.uk.