Diastereoselective synthesis of highly substituted polycyclic scaffolds via a one-pot four-step tandem catalytic process

Grafton, M., Johnson, S. A., Farrugia, L. J. and Sutherland, A. (2014) Diastereoselective synthesis of highly substituted polycyclic scaffolds via a one-pot four-step tandem catalytic process. Tetrahedron Letters, 70(40), pp. 7133-7141. (doi: 10.1016/j.tet.2014.06.020)

Abstract

A rapid and diastereoselective synthesis of highly substituted aminobicyclo[4.3.0]nonanes and bicyclo[4.4.0]decanes from alkyne derived allylic alcohols has been developed using a one-pot multi-bond forming tandem catalytic process. Overman rearrangement of the allylic trichloroacetimidates was followed by a ring closing enyne metathesis/cross metathesis sequence of reactions, in which both steps were catalysed by Grubbs second generation catalyst. The resulting exo-diene was then subjected to a hydrogen bonding directed Diels–Alder reaction forming an endo-adduct as a single diastereomer. Variation of the cross metathesis partner and dienophile allowed examination of the scope of this one-pot process and the preparation of a diverse series of highly substituted polycyclic scaffolds.

• Item Type: Articles
• Status: Published
• Refereed: Yes
• Glasgow Author(s) Enlighten ID: Grafton, Mr Mark and Farrugia, Dr Louis and Sutherland, Professor Andrew
• Authors: Grafton, M., Johnson, S. A., Farrugia, L. J., and Sutherland, A.
• College/School: College of Science and Engineering > School of Chemistry
• Journal Name: Tetrahedron Letters
• Publisher: Elsevier Ltd.
• ISSN: 0040-4039
• ISSN (Online): 1873-3581