title: 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.
authors.affiliation: WestCHEM, School of Chemistry, The Joseph Black Building, University of Glasgow, Glasgow G12 8QQ, UK. Andrew.Sutherland@glasgow.ac.uk.
authors.forename: Mohamed A B
authors.initials: MA
authors.lastname: Mostafa
authors.affiliation: WestCHEM, School of Chemistry, The Joseph Black Building, University of Glasgow, Glasgow G12 8QQ, UK. Andrew.Sutherland@glasgow.ac.uk.
authors.forename: Mark W
authors.initials: MW
authors.lastname: Grafton
authors.affiliation: WestCHEM, School of Chemistry, The Joseph Black Building, University of Glasgow, Glasgow G12 8QQ, UK. Andrew.Sutherland@glasgow.ac.uk.
authors.forename: Claire
authors.initials: C
authors.lastname: Wilson
authors.affiliation: WestCHEM, School of Chemistry, The Joseph Black Building, University of Glasgow, Glasgow G12 8QQ, UK. Andrew.Sutherland@glasgow.ac.uk.
authors.forename: Andrew
authors.initials: A
authors.lastname: Sutherland