Developments in the Field of Aza-Diels-Alder Reactions, Catalytic Michael Additions and Automated Synthesis

Detta är en avhandling från Uppsala : Acta Universitatis Upsaliensis

Sammanfattning: The development of new aza-bicyclic structures with potential applications as ligands synthesised via an aza-Diels-Alder cycloaddition has been studied. The studies are concerning the i) development of large scale aza-Diels-Alder reaction, ii) development of a fast and simple route to bicyclic diamine ligands, iii) development of new aza-Diels-Alder adducts from different dienes, iv) development and application of bicyclic N,P ligands for catalytic Michael additions and v) development of robotized asymmetric transfer hydrogenation reactions.i) Development of large-scale aza-Diels-Alder reaction giving up to 110 g pure product, in ordinary laboratory equipment without the need of any flash chromatography.ii) Development of a new synthetic route to bicyclic diamine ligands highly useful for asymmetric rearrangement of olefin oxides to allylic alcohols and thereby shortening the ligand synthesis dramatically and moreover providing with a faster access to those ligands.iii) Expanding the scope of the aza-Diels-Alder reaction by the use of spirodienes and anthracene as dienes.iv) Development and application of a new bidentate ligands for catalytic Michael addition to cyclic enones using 5 mol % ligand giving the product in 71 % ee.v) Utilisation of Chemspeed ASW 2000 in catalytic transfer hydrogenation and solving of problems regarding use of highly air sensitive reactions in an automated environment.