Synthesis of amino substituted indanes and tetralins via consecutive multi-bond forming tandem processes

Grafton, M. W., Farrugia, L. J. and Sutherland, A. (2013) Synthesis of amino substituted indanes and tetralins via consecutive multi-bond forming tandem processes. Journal of Organic Chemistry, 78(14), pp. 7199-7207. (doi: 10.1021/jo401182r)

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Publisher's URL: http://dx.doi.org/10.1021/jo401182r

Abstract

A rapid and general approach for the synthesis of amino substituted indanes and tetralins from readily available alkyne derived allylic alcohols via consecutive multi-bond forming tandem processes has been developed. In the first one-pot tandem process, a series of cyclic dienes were prepared using an Overman rearrangement under thermal conditions, followed by a ruthenium(II)-catalyzed ring closing enyne metathesis reaction. The resulting exo-dienes were then subjected to a second one-pot tandem process involving a highly regioselective Diels-Alder reaction with alkynes, quinones or nitriles and a subsequent oxidation step to give a diverse library of C-1 amino substituted indanes and tetralins in good overall yields.

Item Type:Articles
Status:Published
Refereed:Yes
Glasgow Author(s) Enlighten ID:Farrugia, Dr Louis and Sutherland, Professor Andrew
Authors: Grafton, M. W., Farrugia, L. J., and Sutherland, A.
College/School:College of Science and Engineering > School of Chemistry
Journal Name:Journal of Organic Chemistry
Publisher:American Chemical Society
ISSN:0022-3263
ISSN (Online):1520-6904

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