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The reductive ring opening of phthalan and isochroman in a 8 mmol scale process, using a small excess of lithium (1.35 equiv) and a substoichiometric amount of DTBB (3 mol%), leads to functionalised organolithium compounds, which after reaction with (-)-menthone as electrophile followed by hydrolysis with water, gives the corresponding diols in good yields with high stereoselectivity. Dehydration of these diols leads to the corresponding oxygen-containing heterocycles, which are homologous of the starting heterocycles.

Reductive Ring Opening of Oxygen-Containing Benzo-Fused Heterocycles by an Arene-Catalysed Lithiation