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Synthesis of Novel Chiral Bicyclic Ligands and their Application in Iridium-Catalyzed Reactions

Title: Digital Comprehensive Summaries of Uppsala Dissertations from the Faculty of Science and Technology
Description:

The synthesis of 2-aza-norborane derivatives is presented. The use of these compounds in preparation of Ir catalysts for asymmetric hydrogenations is described. The evaluation and optimization of the catalysts as well as the mechanistic aspects of the catalytic process are discussed.

The use of non-activated iminodieniphiles in stereoselective aza-Diels-Alder reaction has expanded the scope of the reaction and provided a convenient root for preparation of 2-aza-norboranes, analogues of which were developed into novel bicyclic 2-aza-norbornyl-oxazoline ligands for Ir-catalyzed asymmetric transfer hydrogenations. Using ths Ir complexes acetophenone was hydrogenated in 79% ee.

2-Aza-norbornyl-oxazolines were also developed into novel N,P-ligands. Resulting phosphine-oxazolines were evaluated in Ir-catalyzed asymmetric hydrogenation of structurally diverse imines and olefins.

Optimization of ligands was performed through: 1) Alteration of the stereoconfiguration at the 5’-position as well as variation of the size and geometry of the substituents at this position; 2) Screening through various phosphine substituents of the ligand. Both directions of optimization reflect on the influence of the ligands’ sterik bulk on stereoselectivity of catalytic process. High performance catalysts were developed for both transformations allowing asymmetric hydrogenation of imines with 92% ee and asymmetric hydrogenation of olefins with 99% ee.

Possible mechanisms for these transformations were suggested based on computational studies. Selectivity model for rationalization of results of Ir-catalyzed olefin hydrogenation also was designed.

; Härtill 4 uppsatser; Diss. (sammanfattning) Uppsala : Uppsala universitet, 2005; filosofie doktorsexamen; degree of Doctor of Philosophy; Doctor philosophiae; Docteur ès lettres; Room B42, BMC, Husargatan 3, Uppsala
Creator:

Trifonova Anna 1974- , Uppsala universitet, Avdelningen för organisk kemi

Contributor: Andersson Pher G. Professor; Lloyd-Jones Guy Professor; Uppsala universitet Teknisk-naturvetenskapliga vetenskapsområdet Kemiska sektionen Kemiska institutionen Avdelningen för organisk kemi
Date: 2005; 2005-05-28T10:15:00; 2005-05-04T15:32:00; http://semium.org/time/2005
Type: science; vet; Other academic; Övrigt vetenskapligt; Annet vitenskapelig; comprehensiveDoctoralThesis; dok; Doctoral thesis, comprehensive summary; Doktorsavhandling, sammanläggning; Doktoravhandling, med artikler; dissertation; text; http://www.eionet.europa.eu/gemet/concept/7472; http://www.eionet.europa.eu/gemet/concept/13026
Format: electronic72; electronic; 72
Identifier: 91-554-6243-X; url: http://urn.kb.se/resolve?urn=urn:nbn:se:uu:diva-5783; 1651-6214; 50
Relation: Digital Comprehensive Summaries of Uppsala Dissertations from the Faculty of Science and Technology1651-621450
Language: eng
Publisher: Acta Universitatis Upsaliensis
Data provider: Uppsala Universitet
Provider: The European Library
Providing country: Sweden

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