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

Mostafa, M. A.B., Grafton, M. W., Wilson, C. and Sutherland, A. (2016) A one-pot, three-step process for the diastereoselective synthesis of aminobicyclo[4.3.0]nonanes using consecutive palladium(II)- and ruthenium(II)-catalysis. Organic and Biomolecular Chemistry, 14(14), pp. 3284-3297. (doi: 10.1039/C6OB00165C) (PMID:26932788)

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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.

Item Type:Articles
Additional Information:Financial support from the Ministry of Higher Education and Scientific Research, Omar Al-Mukhtar University, Libya (studentship to M.A.B.M.) and the University of Glasgow (University Scholarship to M.W.G.) is gratefully acknowledged. We thank the EPSRC UK National Crystallography Service at the University of Southampton for the collection of the crystallographic data.
Status:Published
Refereed:Yes
Glasgow Author(s) Enlighten ID:Wilson, Dr Claire and Mostafa, Mohamed and Sutherland, Dr Andrew
Authors: Mostafa, M. A.B., Grafton, M. W., Wilson, C., and Sutherland, A.
College/School:College of Science and Engineering > School of Chemistry
Journal Name:Organic and Biomolecular Chemistry
Publisher:Royal Society of Chemistry
ISSN:1477-0520
ISSN (Online):1477-0539
Published Online:25 February 2016
First Published:First published in Organic and Biomolecular Chemistry 14(12):3284-3297
Publisher Policy:Reproduced under a Creative Commons License

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