Substituted tetrahydropyrans are important structural motifs in many of the complex natural products, and Prins cyclization is one of the important synthetic tool for assembling this motif. Recently, Oxidative Prins cyclization has been utilized to construct tetrahydropyrans that uses ethers instead of unstable aldehydes. In this respective research, we carried out Prins cyclization of benzyl ethers with DDQ and various Lewis acid combinations, untill dated there was only one reported reaction on intramolecular Prins/Friedal-Crafts cyclization that utilizes stoichiometric amount of DDQ along with catalytic toxic tin (IV) chloride. The goal of my research project is to identify a stable, nontoxic and environmentally friendly Lewis acid catalyst without compromising in the yield and selectivity. This dissertation presents screening of Lewis acids and optimization of reaction conditions as well.
January 30, 2015
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