Issue 12, 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

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

Supplementary files

Article information

Article type
Paper
Submitted
19 Jan 2016
Accepted
25 Feb 2016
First published
25 Feb 2016
This article is Open Access
Creative Commons BY license

Org. Biomol. Chem., 2016,14, 3284-3297

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

This article is licensed under a Creative Commons Attribution 3.0 Unported Licence. You can use material from this article in other publications without requesting further permissions from the RSC, provided that the correct acknowledgement is given.

Read more about how to correctly acknowledge RSC content.

Social activity

Spotlight

Advertisements