ISBN 9783843927734

978-3-8439-2773-4, Reihe Organische Chemie

Thomas Gilles
Asymmetric Synthesis of N-Allylic Indoles via Regio- and Enantioselective N-Allylation of Arylhydrazines / Regio- and Enantioselective Hydroformylation of 7-Hetero-Bridged Benzonorbornadiene Derivatives

381 Seiten, Dissertation Albert-Ludwigs-Universität Freiburg im Breisgau (2016), Softcover, A5

Zusammenfassung / Abstract

The present dissertation deals with two methodology projects:

1) The development and optimization of a regio- and enantioselective rhodium-catalyzed addition of aryl hydrazines onto allenes toward branched N-allylic hydrazines. As indoles can be synthesized via phenyl hydrazine intermediates, a new “two steps/one pot” methodology for the access of N-allylic indoles by this rhodium catalyzed pathway was of great interest and was therefore investigated. Both of these goals were successfully achieved and various asymmetric N-allylic hydrazines, as well as N-allylic indoles were obtained with high yield, regio- and enantioselectivity.

2) The second project of this PhD work was a contribution to the field of hydroformylation. Investigation of the yet unstudied hydroformylation of 7-hetero-bridged benzonorbornadiene substrates using newly reported ligands developed within the Breit group was conducted. Screening for this reaction, as well as synthesis of these ligand derivatives were performed. Further additional investigations and variations of these ligand type are still under investigation.