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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 ISSN 0040-4039.
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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 | ||||
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Subjects: | Q Science > QD Chemistry | ||||
Divisions: | Faculty of Science, Engineering and Medicine > 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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