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Palladium and copper-catalysed (C-C)-bond formation

Bulic, Bruno. Palladium and copper-catalysed (C-C)-bond formation. 2006, Doctoral Thesis, University of Basel, Faculty of Science.

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Official URL: http://edoc.unibas.ch/diss/DissB_7524

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Abstract

Copper-Catalysed Conjugate Additions:
Conjugate 1,4-additions of carbon nucleophiles to α,β-unsaturated ketones are valuable C-C bond forming reactions that furthermore allow introduction of stereogenic centers.(1) Copper-catalysed reactions have been successfully employed in a variety of syntheses, for example for (-)-solavetivone(2) or prostaglandins.(3) Improvement of enantioselectivity through design of more effective ligands is thus highly desirable.
The ligands depicted below were synthesised and tested, with excellent enantioselectivities on selected substrates.
Muscone Synthesis:
Musk odorants are a family of molecules possessing a very nice smell, of central importance for the fragrance industry. Application of the methodology developed for the copper-catalysed conjugate addition to the synthesis of (S)-muscone allowed the obtaining of product 90 in high yield and excellent enantiomeric purity.
Multicomponent Heck-Allylic substitution Reaction:
Synthetic methodology which allows for a rapid increase in molecular complexity is extremely valuable in organic chemistry, particularly if it generates more than one new carbon-carbon bond at a time, accommodates considerable functionality and is broad in scope.
Design of a reaction sequence involving a Heck reaction followed by an allylic substitution allowed the obtaining of compound 141 depicted below.
Advisors:Pfaltz, Andreas
Committee Members:Wennemers, Helma
Faculties and Departments:05 Faculty of Science > Departement Chemie > Chemie > Synthetische organische Chemie (Pfaltz)
UniBasel Contributors:Pfaltz, Andreas and Wennemers, Helma
Item Type:Thesis
Thesis Subtype:Doctoral Thesis
Thesis no:7524
Thesis status:Complete
Bibsysno:Link to catalogue
Number of Pages:182
Language:English
Identification Number:
Last Modified:22 Jan 2018 15:50
Deposited On:13 Feb 2009 15:36

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