A new catalytic method for the synthesis of highly substituted tetrahydrofurans via cycloaddition reactions of alkenes and alkenols will be presented. Current intermolecular methodologies capable of yielding such heterocycles employ either highly pre-functionalized substrates or rely on transition metal catalysis. We will be presenting the outcome of a strategy that effectively couples simple, readily available olefins and alkenols via a polar-radical crossover cyclization, catalyzed by an organic photoredox system. This strategy affords high-value tetrahydrofuran rings with up to four contiguous stereocenters in a cycloaddition process that forges three new bonds. The proposed mechanism of this transformation will be discussed.

Synthesis of tetrahydrofurans via polar-radical crossover cyclization

245th National Meeting (2013)

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