The Oxidation-Initiated Nazarov Cyclization and Other Pericyclic Transformations

• Author / Creator

  Schmidt, Emily

• The synthesis of interesting and useful cyclic structures is of high importance in chemistry. Strategies for their synthesis include pericyclic reactions, namely electrocyclizations and cycloadditions. This thesis will discuss the investigation towards the synthesis of cyclic structures via Nazarov cyclization, as well as a catalytic thermal [2+2] cycloaddition.
  Chapter 1 describes recent advances in the Nazarov cyclization. A growing area is the use of non-traditional reagents to activate the divinyl ketone and derivatives towards cyclization. This provides alternative and sometimes milder conditions for the reaction. Another area of interest is the use of non-traditional substrates in the Nazarov cyclization, allowing access to interesting novel products.
  Chapter 2 describes efforts towards the oxidation-initiated cyclization of non-traditional Nazarov substrates, such as silyl enol ethers and allylic ethers. Interestingly, products of these reactions when using DDQ as the oxidant resulted in DDQ adduct structures, via Diels-Alder reaction.
  Chapter 3 describes the development of a catalytic Lewis acid mediated formal [2+2] cycloaddition of o-styrenyl chalcones, forming bicyclic structures. A preliminary investigation into an asymmetric transformation is also presented.

• Subjects / Keywords

  • Nazarov
  • Electrocyclization
  • Cycloaddition
  • Lewis Acid

• Graduation date

  Fall 2024

• Type of Item

  Thesis

• Degree

  Master of Science

• DOI

  https://doi.org/10.7939/r3-b8kv-8948

• License

  This thesis is made available by the University of Alberta Library with permission of the copyright owner solely for non-commercial purposes. This thesis, or any portion thereof, may not otherwise be copied or reproduced without the written consent of the copyright owner, except to the extent permitted by Canadian copyright law.