Asymmetric synthesis of heterocycles via cation-directed cyclizations and rearrangements

Thesis

The aim of this project was to utilize chiral cation-directed catalysis in the asymmetric synthesis of novel hererocycles. This goal was initially realized by the synthesis of azaindolines in high yields and enantioselectivities (Chapter 2).

Extension of this methodology to substrates bearing two stereogenic centres was successful, although control over both diastereoselectivity and enantioselectivity in this process was modest.

Finally the synthesis of heterocycles utilizing cation-directed rearrangement processes was examined, with proof of concept obtained for a novel asymmetric cyclization to form xanthenes.

Authors: Lamb, A; Alan Lamb

• Publication date: 2014
• DOI: 10.5287/ora-007qkaxmg
• Type of award: DPhil
• Level of award: Doctoral
• Awarding institution: Oxford University, UK
• Language: English
• Keywords: methodology; phase-transfer catalysis; Asymmetric catalysis
• Subjects: Synthetic organic chemistry