Rapid generation of molecular complexity under Pd(II) and Rh(III) catalysis
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Date
26/11/2015Author
Kujawa, Szymon
Metadata
Abstract
1. Enantioselective Pd(II)-Catalysed Nucleophilic Additions of 2-
Alkylazaarenes
The first project deals with enantio- and diastereoselective palladium(II)-catalysed
nucleophilic additions of 2-alkylazaarenes to N-Boc imines and nitroalkenes. Under
the optimised reaction conditions high levels of diastereo- and enantioselection of the
addition products were achieved. Introduction of the electron-withdrawing group at
the aryl ring of the substrate allows running the reaction under mild, experimentally
convenient reaction conditions. The new described method allows the
enantioselective synthesis of 2-(β-aminoalkyl)azaarenes, which are substructures
found in drug candidates molecules for the treatment of type 2 diabetes and
schizophrenia. 2. Synthesis of Spirocyclic Enones via Rh(III)-Catalysed C–H
Functionalisation
The second project describes the synthesis of spirocyclic enones by rhodium(III)-
catalysed dearomatising oxidative annulation of 2-alkenylphenols with alkynes and
1,3-enynes. A good to high yield with great regioselectivity was obtained. The
further synthetic utility of the product was also investigated and led to the formation
of highly functionalised tetracycles via 1,6 conjugation addition reaction.