The 1,6-conjugate addition initiated nazarov and 1,5-hydride transfer initiated cascade cyclization

Thesis (Ph. D.)--University of Rochester. Department of Chemistry, 2019.The iodoaldol reaction can generate densely functionalized iodoallylic alcohols which can be further functionalized under acidic conditions to affect cyclization reactions. This reaction can be conducted in both an intermolecular and intramolecular fashion. This process has the potential to rapidly introduce functionality and structural complexity into a system from simple starting materials. The 1,6-conjugate addition initiated Nazarov (1,6-CAIN) reaction allows us to rapidly generate highly stereodefined cyclopentenones, which are then able to undergo further transformations. The 1,6-CAIN sets up a 1,5-Hydride transfer / oxyallyl cation formation / Friedel-Crafts cyclization cascade sequence which allows for the formation of bridged N-heterocycles