Stereocontrolled approach to 1-azabicyclo[4.1.0]heptanes: application to the synthesis of trans-2,6-disubstituted piperidines |
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Authors: | Emma L Wynne |
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Institution: | Department of Chemistry, University of Warwick, Gibbet Hill Road, Coventry CV4 7AL, UK |
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Abstract: | Stereocontrolled synthesis of a 1-azabicyclo4.1.0]heptane is achieved by formation of an NH aziridine from the corresponding 1,2-azido alcohol and subsequent intramolecular conjugate addition onto a tethered α,β-unsaturated ester. Regioselective ring opening of the product at C-7 by heteroatom based nucleophiles yields trans-2,6-disubstituted piperidines in moderate to good yields. |
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Keywords: | Nitrogen heterocycles Strained compounds Ring opening 1-Azabicyclo[4 1 0]heptanes Piperidines |
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