Intramolecular ring opening of epoxides by bis-activated carbanions. The influence of ring size on reactivity and selectivity

Cyclization is the common synthetic method for ring compounds from micro to macrocycles. The method is especially useful in difunctional molecules with nucleophilic centers where epoxide cyclization through intramolecular ring openings forms cyclic alcohol. The regioselectivity of the intramolecular ring depends on substituent stereochemistry in the three member ring, and is controlled by experimental modification and structure of the substrate.