Chiral cation-directed asymmetric 5-endo-trig cyclizations

Thesis

The primary objective of this research project was to develop a novel protocol for the synthesis of densely functionalized optically enriched indanes through a chiral cation directed 5-endo-trig ring closure. In chapter two, a convergent strategy for the construction of the cyclization precursors is reported, which employs two easily adapted fragments. In chapter three, a range of quaternary ammonium salts are screened to establish the optimal phase-transfer conditions for this system. A variety of substrates were evaluated to probe the scope and limitations of this methodology. Finally, two potential mechanistic pathways for this enigmatic process are outlined and discussed in chapter four.

Authors: Johnston, CP

• Publication date: 2013
• Type of award: DPhil
• Level of award: Doctoral
• Awarding institution: University of Oxford
• Language: English
• Keywords: catalysis; phase-transfer catalysis; asymmetric; cyclization; Baldwin's rules; indanes; organic chemistry
• Subjects: Synthetic organic chemistry; Chemistry & allied sciences; Organic chemistry; Asymmetric catalysis; Physical Sciences; Organic synthesis; Catalysis