Synthesis of Tertiary Alcohols via an Ionic Liquid Catalyst
By Jeanne L. Kuhler, Robey T. Brooks, Whitney K. Helms, Krystal D. Holley, Pratik P. Patel, Candace Phillips, Tiffany R. Shorter
The core of furans has been found to be present in many pharmaceuticals, such as polyether antibiotics, as well as flavors and fragrances, optoelectronics, and many natural products with therapeutic potential. A similar class of compounds called the 2-pyrones has been reported to be vital in natural products with antimicrobial, antifungal, and anti-HIV effects. Despite their usefulness, current synthetic approaches are limited. One method used to synthesize furans is the intramolecular cyclization of ynols via a 5-endo cyclocondensation mechanism. Cyclocondensation reactions offer the advantage of occurring in one step and thus prevent the isomerization and resulting regioselectivity problems associated with multi-step reactions. In order to complete these cyclocondensation reactions we have used a new environmentally safer ionic liquid catalyst in the Grignard reaction to prepare several ynols and additional tertiary alcohols.
Keywords :catalyst, ionic liquids, alcohols, ynols, Grignard reagent, pharmaceuticals