A one-pot, three-step process for the diastereoselective synthesis of aminobicyclo[4.3.0]nonanes using consecutive palladium(ii)- and ruthenium(ii)-catalysis. Issue 12 (2nd March 2016)

• Record Type: Journal Article
• Authors: Mostafa, Mohamed A. B.; Grafton, Mark. W.; Wilson, Claire; Sutherland, Andrew
• Is Part Of: Organic & biomolecular chemistry. Volume 14:Issue 12(2016)
• Page Start: 3284
• Page End: 3297
• Publication Date: 2016-03-02
• Subjects: Chemistry, Organic -- Periodicals; Bioorganic chemistry -- Periodicals; Chemistry, Physical organic -- Periodicals; 547
• DOI: 10.1039/c6ob00165c
• Languages: English
• ISSNs: 1477-0520

Abstract

Abstract : A one-pot multi-step process that uses both Pd(ii )- and Ru(ii )-catalysis has been developed for the diastereoselective synthesis of aminobicyclo[4.3.0]nonanes. 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.