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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. 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

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:

Page Range:

pp. 250-252

Identification Number:

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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