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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

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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:
DateEvent
7 January 2008Published
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

Data sourced from Thomson Reuters' Web of Knowledge

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