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Pd(II) - Catalysed Cyclisations of Aminoalkenitols

Pd(II) - Catalysed Cyclisations of Aminoalkenitols. Dr. Peter Szolcsányi Department of Organic Chemistry S lovak U niversity of Technology Bratislava , Slovak Republic. Pd(II)-Catalysed chlorocyclisation and N , O -bicyclisation of polyhydroxylated aminoalkenitols.

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Pd(II) - Catalysed Cyclisations of Aminoalkenitols

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  1. Pd(II)-Catalysed Cyclisationsof Aminoalkenitols Dr. Peter Szolcsányi Department of Organic Chemistry Slovak University of Technology Bratislava, Slovak Republic

  2. Pd(II)-Catalysed chlorocyclisation and N,O-bicyclisation of polyhydroxylated aminoalkenitols

  3. Synthetic versatility of chloromethyl piperidines

  4. Structural diversity of piperidine/azepine alkaloids

  5. Where did the idea come from ? P. Szolcsányiet al.: Tetrahedron: Asymmetry 2000, 11, 2579-2597.

  6. Substrates for the screening

  7. Preparation of substrates - D-glucoserie

  8. Preparation of substrates - D-galactoserie

  9. Pd(II)/CuCl2-catalysed chlorocyclisation-D-gluco serie

  10. Pd(II)/CuCl2-catalysed chlorocyclisation-D-galacto serie

  11. Mechanistic proposal of the Pd(II)/CuCl2-catalysed chloroaminocyclisation and bicyclisation

  12. Synthesis of new analogues of iminoalditols P. Szolcsányi, T. Gracza: Tetrahedron 2006, 62, 8498-8502.

  13. Conclusions • We have found a novel Pd(II)-catalysed halocyclisation and/or bicyclisation • of aminoalkenitols providing chloromethyl-piperidines and/or oxa- • azabicyclo[3.2.1]octanes • We have postulated the reaction mechanism explaining the observed • chemoselectivity • Both transformations were developed intoeffectivesynthetic methodologies • that were successfully employed in the total synthesis of new analogues of • glycosidase inhibitor 1-deoxynojirimycin

  14. Acknowledgments Generous support Prof. Dr. Tibor Gracza HPLC Dr. Katarína Hroboňová NMR Dr. Naďa Prónayová IR Ms. Silvia Markusová MALDI Dr. Ivan Špánik Grant APVT-20-000904

  15. Known precedents of Pd(II)/CuCl2-catalysed haloaminocyclisation yielding 6-membered azacycles

  16. Known reports on Pd(II)/Cu(II)-heterobimetallic complexes

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