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Full Paper
Asymmetric Synthesis of Aminocyclopropanes and N-Cyclopropylamino Alcohols Through Direct Amidocyclopropanation of Alkenes Using Chiral Organozinc Carbenoids
Article first published online: 23 FEB 2009
DOI: 10.1002/ejoc.200801033
Copyright © 2009 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim
Additional Information
How to Cite
Bégis, G., Cladingboel, D. E., Jerome, L., Motherwell, W. B. and Sheppard, T. D. (2009), Asymmetric Synthesis of Aminocyclopropanes and N-Cyclopropylamino Alcohols Through Direct Amidocyclopropanation of Alkenes Using Chiral Organozinc Carbenoids. European Journal of Organic Chemistry, 2009: 1532–1548. doi: 10.1002/ejoc.200801033
Publication History
- Issue published online: 13 MAR 2009
- Article first published online: 23 FEB 2009
- Manuscript Received: 22 OCT 2008
Funded by
- Engineering and Physical Sciences Research Council (EPSRC)
- AstraZeneca
- Abstract
- Article
- References
- Cited By
Keywords:
- Cyclopropanes;
- Chiral auxiliaries;
- Alkenes;
- Carbenoids;
- Zinc
Graphical Abstract
A versatile method is described for the synthesis of a range of enantiopure amino- and amido-cyclopropanes, through the generation of organozinc carbenoids from N-(diethoxymethyl)oxazolidinones.
Abstract
Chiral N-(diethoxymethyl)oxazolidinones, prepared from the corresponding oxazolidinones by heating in triethyl orthoformate, can be used as organozinc carbenoid precursors for the direct enantioselective amidocyclopropanation of alkenes. The reaction is successful with a wide range of oxazolidinones and alkenes and proceeds with moderate to excellent yield and stereoselectivity. In most cases the trans/exo amidocyclopropane product is favoured, although certain cyclicalkenes such as indene favour the formation of the endo cyclopropane. The products can be readily elaborated to produce cyclopropylamino alcohols and amino acids.(© Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2009)