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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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:	Date Event 7 January 2008 Published
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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