Novel axially chiral amines as organocatalysts

Kinsey, Francesca (2016) Novel axially chiral amines as organocatalysts. Doctoral thesis, University of East Anglia.

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Novel axially chiral amines as organocatalysts
Keywords: Axial chirality, asymmetric organocatalysis, Reformatsky reaction, Diels-
Alder reaction, amino acid.
This body of research describes the recent developments our group has contributed towards the synthesis of novel axially chiral α- and β-functionalized amino acids and their application in asymmetric catalysis. This thesis is divided into three sections.
The first chapter contains a review of the discovery and development of
organocatalysis and includes key examples of its progression in terms of widening applications and improving selectivities.
The second chapter consists of the results and discussion section of this thesis and it is divided into two parts. Part one contains works relating to the synthesis of a series of binaphthyl and biphenyl organocatalysts and describes key selective synthetic steps: a diastereoselective Reformatsky addition and asymmetric lithiation and chloroformate/carboxylation addition steps. Part two focuses on the observed enantio- and diastereoselectivity of these catalysts in the aldol, Michael and Diels- Alder reactions.
Key steps: i) 10 mol% 239.HCl, MeOH:H2O, 0 °C ii) LiAlH4 reduction
Section three contains the experimental data for the compounds described in chapter two.

Item Type: Thesis (Doctoral)
Faculty \ School: Faculty of Science > School of Chemistry
Depositing User: Megan Ruddock
Date Deposited: 16 May 2018 15:58
Last Modified: 16 May 2018 15:58

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