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Issue 12, 2016
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A one-pot, three-step process for the diastereoselective synthesis of aminobicyclo[4.3.0]nonanes using consecutive palladium(ii)- and ruthenium(ii)-catalysis

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Abstract

A diastereoselective synthesis of highly substituted aminobicyclo[4.3.0]nonanes has been attained using a one-pot multi-bond forming process. A four-step synthetic route was developed for the efficient synthesis of a series of C-7 substituted hept-2-en-6-yn-1-ols. These compounds were then investigated as substrates for a one-pot, three-step tandem process involving a palladium(II)-catalysed Overman rearrangement, a ruthenium(II)-catalysed ring closing enyne metathesis reaction followed by a hydrogen bond directed Diels–Alder reaction. The optimisation of the one-pot process has allowed the rapid preparation of a library of aminobicyclo[4.3.0]nonanes with significant molecular complexity and up to four stereogenic centres.

Graphical abstract: A one-pot, three-step process for the diastereoselective synthesis of aminobicyclo[4.3.0]nonanes using consecutive palladium(ii)- and ruthenium(ii)-catalysis

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Supplementary files

Article information


Submitted
19 Jan 2016
Accepted
25 Feb 2016
First published
25 Feb 2016

This article is Open Access

Org. Biomol. Chem., 2016,14, 3284-3297
Article type
Paper
Author version available

A one-pot, three-step process for the diastereoselective synthesis of aminobicyclo[4.3.0]nonanes using consecutive palladium(II)- and ruthenium(II)-catalysis

M. A. B. Mostafa, Mark. W. Grafton, C. Wilson and A. Sutherland, Org. Biomol. Chem., 2016, 14, 3284
DOI: 10.1039/C6OB00165C

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