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The aldol addition-pinacol rearrangement sequence starting with 1,2-bis(trimethylsilyloxy)cyclobutene and a ketal or acetal provides facile entry into a series of substituted 1,3-cyclopentadiones.2 This, combined with the known propensity for 1,3-diketones to undergo cleavage reactions, affords a useful sequence for the synthesis of γ-ketocarboxylic acids:
Application of this sequence is demonstrated in a new synthesis of 2,3-dihydrobenzo [b] furan (ergo, benzo[b] furan).
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