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The aza-Diels-Alder reaction protocol - a useful approach to chiral, sterically constrained alpha-amino acid derivatives
Uppsala University, Teknisk-naturvetenskapliga vetenskapsområdet, Chemistry, Department of Chemistry.
2001 In: Tetrahedron, ISSN 0040-4020, Vol. 57, no 30, 6399-6406 p.Article in journal (Refereed) Published
Place, publisher, year, edition, pages
2001. Vol. 57, no 30, 6399-6406 p.
Identifiers
URN: urn:nbn:se:uu:diva-92315OAI: oai:DiVA.org:uu-92315DiVA: diva2:165344
Available from: 2004-10-26 Created: 2004-10-26Bibliographically approved
In thesis
1. Developments in the Field of Aza-Diels-Alder Reactions, Catalytic Michael Additions and Automated Synthesis
Open this publication in new window or tab >>Developments in the Field of Aza-Diels-Alder Reactions, Catalytic Michael Additions and Automated Synthesis
2004 (English)Doctoral thesis, comprehensive summary (Other academic)
Abstract [en]

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.

Place, publisher, year, edition, pages
Uppsala: Acta Universitatis Upsaliensis, 2004. 48 p.
Series
Comprehensive Summaries of Uppsala Dissertations from the Faculty of Science and Technology, ISSN 1104-232X ; 1032
Keyword
Organic chemistry, Asymmetric synthesis, aza-Diels-Alder, Michael addition, Transfer hydrogenation, automated synthesis, Catalysis, Organisk kemi
National Category
Organic Chemistry
Identifiers
urn:nbn:se:uu:diva-4640 (URN)91-554-6076-3 (ISBN)
Public defence
2004-11-19, B41, BMC, Husargatan 3, Uppsala, 13:15
Opponent
Supervisors
Available from: 2004-10-26 Created: 2004-10-26Bibliographically approved

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