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ISBN 9783843922463

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978-3-8439-2246-3, Reihe Organische Chemie

Philipp Koschker
Rhodium-Catalyzed Hydro-Oxycarbonylation of Alkynes and Allenes: New Asymmetric Access to Branched Allylic Esters

329 Seiten, Dissertation Albert-Ludwigs-Universität Freiburg im Breisgau (2015), Softcover, A5

Zusammenfassung / Abstract

Enantioenriched branched allylic esters are essential building blocks for organic synthesis. This dissertation details the development and optimization of a new Rhodium-catalyzed coupling of terminal alkynes and allenes with carboxylic acids. These processes are understood as an emerging and highly efficient way of accessing this substrate class.

By means of phosphorus ligand synthesis and screening as well as extensive reaction condition optimizations, highly selective and general methodologies could be developed. Their utility for synthesis was shown by demonstrating their high functional group tolerance and scalability. Additionally, short three-step syntheses of naturally occurring whisky and cognac lactone were performed.