Chemo and enantioselective addition of grignard reagents to ketones and enolizable ketimines

Pablo Ortiz

Research output: ThesisThesis fully internal (DIV)

1370 Downloads (Pure)

Abstract

The geometrical disposition of atoms in space can have a crucial role on the effect that a molecule exerts in an organism. In the same way that the right hand will fit in a right glove but not in a left glove, the 3D disposition of atoms in a molecule determines how that molecule will interact with others. Molecules that are not superimposable with their mirror image (like our hands) are termed chiral, from the Greek name for "hand". The synthesis of chiral molecules is important in a variety of fields, and paramount significance in pharmaceuticals or crop protection agents preparation.

In most of the cases these molecules contain oxygen and nitrogen groups, often in the form of alcohols (-OH group) and amines (-NH2) groups. The goal of this thesis has been to develop a straightforward methodology to access a particular set of these molecules which are difficult to make in the laboratory: chiral α-tertiary alcohols and amines. The main scientific contribution has been the delivery of a methodology that enables their preparation from easy to synthesize or commercially available materials and Grignard reagents. The latter are very reactive compounds, but using copper as a catalyst their high reactivity could be harnessed.

Besides, the rearrangement (reposition of the atoms in a molecule) of some of those compounds has been studied. Finally, the structure of the Grignard reagents in uncommon solvents has been investigated using NMR (Nuclear Magnetic Resonance).
Original languageEnglish
QualificationDoctor of Philosophy
Awarding Institution
  • University of Groningen
Supervisors/Advisors
  • Harutyunyan, Syuzanna, Supervisor
  • Browne, Wesley, Supervisor
Award date3-Oct-2017
Place of Publication[Groningen]
Publisher
Print ISBNs978-94-6299-708-0
Electronic ISBNs978-94-6299-710-3
Publication statusPublished - 2017

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