Development of Axially Chiral Biazulenes for Catalysis

  • Anthony Gee

Student thesis: Doctoral ThesisPhD

Abstract

Axially chiral biaryl ligands are ubiquitious in asymmetric transition metal-catalysed homogeneous catalysis. However, biazulene motifs have not previously been incorporated in the design of chiral ligands in asymmetric catalysis, despite the unique geometric and electronic properties of azulene derivatives. The aims of this project were to develop novel axially chiral biazulene-diphosphine, -diol and related species, encompassing the synthesis and resolution of their enantiomers, and to screen these compounds in the application towards common asymmetric reactions.The most significant achievement reached in this project was the synthesis andresolution of practicable quantities of an atropisomeric 1,1’-biazulene-2,2’-diolspecies (“1,1’-BazOL”), which has been employed in an asymmetric Ti-catalysedDiels–Alder reaction. Much progress has also been made towards the synthesis of other targets, like 1,1’-biazulene-2,2’-diphosphine (“1,1’-BazPhos”), 2,2’-biazulene-1,1’-diphosphine (“2,2’-BazPhos”) and 1,1’-biazulene-2,2’-phosphoric acid (“1,1’-BazPA”).
Date of Award23 Nov 2016
Original languageEnglish
Awarding Institution
  • University of Bath
SponsorsEngineering and Physical Sciences Research Council
SupervisorSimon Lewis (Supervisor)

Cite this

Development of Axially Chiral Biazulenes for Catalysis
Gee, A. (Author). 23 Nov 2016

Student thesis: Doctoral ThesisPhD