Activation of -Propargyl Alcohol Benzaldehydes under Acetalization Conditions for Intramolecular Electrophile Intercepted Meyer-Schuster Rearrangement.

The reactivity of -propargyl alcohol benzaldehydes has been increased tremendously toward Brønsted acid-catalyzed intramolecular electrophile intercepted Meyer-Schuster (M-S) rearrangement under acetalization conditions using trimethyl orthoformate (TMOF). The in situ formed acetal transfers the methoxy group intramolecularly to generate the M-S intermediate in even less reactive substrates, and the formed oxocarbenium ion makes the carbonyl more electrophilic for an effective intramolecular trapping of the M-S intermediate to furnish the indanone derivatives.