Synthesis of Nitrogen-Containing Heterocycles through Catalytic Dehydrative Cyclization Reactions

Re2O7 in hexafluoroisopropyl alcohol provides access to cationic intermediates from alcohols through the intermediacy of perrhenate esters. This manuscript describes the application of the system to the formation of a number of weakly basic heterocyclic systems through dehydration reactions and intramolecular nucleophilic addition. The influence of the substrate structure on the reaction rates and stereocontrol is discussed with respect to intermediate ion pairs.

Automated summary

This manuscript describes a method in which Re2O7 in hexafluoroisopropyl alcohol converts alcohols into cationic intermediates through perrhenate esters, and discusses its application in the formation of weakly basic heterocyclic systems. The influence of the substrate structure on reaction rates and stereocontrol is also discussed.