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Stereocontrolled approach to 1-azabicyclo[4.1.0]heptanes : application to the synthesis of trans-2,6-disubstituted piperidines
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Wynne, Emma L., Clarkson, Guy J. and Shipman, Michael (2008) Stereocontrolled approach to 1-azabicyclo[4.1.0]heptanes : application to the synthesis of trans-2,6-disubstituted piperidines. Tetrahedron Letters, Volume 49 (Number 2). pp. 250-252. doi:10.1016/j.tetlet.2007.11.077
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Official URL: http://dx.doi.org/10.1016/j.tetlet.2007.11.077
Abstract
Stereocontrolled synthesis of a 1-azabicyclo[4.1.0]heptane is achieved by formation of an NH aziridine from the corresponding 1.2-azido alcohol and subsequent intramolecular conjugate addition onto a tethered alpha,beta-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. (c) 2007 Elsevier Ltd. All rights reserved.
| Item Type: | Journal Article | ||||
|---|---|---|---|---|---|
| Subjects: | Q Science > QD Chemistry | ||||
| Divisions: | Faculty of Science > Chemistry | ||||
| Library of Congress Subject Headings (LCSH): | Heterocyclic compounds, Nitrogen, Ring-opening polymerization, Stereochemistry, Aziridines | ||||
| Journal or Publication Title: | Tetrahedron Letters | ||||
| Publisher: | Elsevier | ||||
| ISSN: | 0040-4039 | ||||
| Official Date: | 7 January 2008 | ||||
| Dates: |
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| Volume: | Volume 49 | ||||
| Number: | Number 2 | ||||
| Number of Pages: | 3 | ||||
| Page Range: | pp. 250-252 | ||||
| DOI: | 10.1016/j.tetlet.2007.11.077 | ||||
| Status: | Peer Reviewed | ||||
| Publication Status: | Published | ||||
| Access rights to Published version: | Restricted or Subscription Access | ||||
| Funder: | Engineering and Physical Sciences Research Council (EPSRC), University of Warwick |
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