Stereoselective synthesis of hydroxylated 3-aminoazepanes using a multi-bond forming, three-step tandem process

Ahmad, S. and Sutherland, A. (2012) Stereoselective synthesis of hydroxylated 3-aminoazepanes using a multi-bond forming, three-step tandem process. Organic and Biomolecular Chemistry, 10(41), pp. 8251-8259. (doi: 10.1039/C2OB26544C)

Abstract

A multi-bond forming, three-step tandem process involving a palladium(II)-catalysed Overman rearrangement and a ring closing metathesis reaction has been utilised for the efficient synthesis of a 2,3,6,7-tetrahydro-3-amidoazepine. Substrate directed epoxidation or dihydroxylation of this synthetic intermediate has allowed the diastereoselective synthesis of hydroxylated 3-aminoazepanes including the syn-diastereomer of the balanol core. Asymmetric synthesis of the 2,3,6,7-tetrahydro-3-amidoazepine motif was also achieved using a chiral palladium(II)-catalyst during the Overman rearrangement.

• Item Type: Articles
• Status: Published
• Refereed: Yes
• Glasgow Author(s) Enlighten ID: Ahmad, Mr Sajjad and Sutherland, Professor Andrew
• Authors: Ahmad, S., and Sutherland, A.
• College/School: College of Science and Engineering > School of Chemistry
• Journal Name: Organic and Biomolecular Chemistry
• ISSN: 1477-0520
• ISSN (Online): 1477-0539
• Published Online: 31 August 2012
• Copyright Holders: Copyright © 2012 The Royal Society of Chemistry
• First Published: First published in Organic & Biomolecular Chemistry 10(41):8251-8259
• Publisher Policy: Reproduced in accordance with the copyright policy of the publisher