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X=Y–ZH compounds as potential 1,3-dipoles. Part 64: Synthesis of highly substituted conformationally restricted and spiro nitropyrrolidines via Ag(I) catalysed azomethine ylide cycloadditions

Grigg, R., Kilner, C., Sarker, M.A.B., Orgaz de la Cierva, C. and Dondas, H.A. (2008) X=Y–ZH compounds as potential 1,3-dipoles. Part 64: Synthesis of highly substituted conformationally restricted and spiro nitropyrrolidines via Ag(I) catalysed azomethine ylide cycloadditions. Tetrahedron, 64 (37). pp. 8974-8991. ISSN 0040-4020

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Abstract

1,3-Dipolar reactions of imines of both acyclic and cyclic α-amino esters with a range of nitroolefins using a combination of AgOAc or Ag2O with NEt3 are described. In most cases the reactions were highly regio- and stereospecific and endo-cycloadducts were obtained in good yield. However, in a few cases the initially formed cycloadducts underwent base catalysed epimerisation. The stereochemistry of the cycloadducts was assigned from NOE data and established unequivocally in several cases by X-ray crystallography.

Item Type: Article
Copyright, Publisher and Additional Information: © 2008 Elsevier B.V This is an author produced version of a paper published in Tetrahedron. Uploaded in accordance with the publisher's self archiving policy.
Academic Units: The University of Leeds > Faculty of Maths and Physical Sciences (Leeds) > School of Chemistry (Leeds)
Depositing User: Sherpa Assistant
Date Deposited: 10 Oct 2008 15:25
Last Modified: 08 Feb 2013 16:56
Published Version: http://dx.doi.org/10.1016/j.tet.2008.05.132
Status: Published
Publisher: Elsevier B.V.
Identification Number: 10.1016/j.tet.2008.05.132
URI: http://eprints.whiterose.ac.uk/id/eprint/4740

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