Pennell, MN; (2014) Gold Catalysed Reactions of Propargylic Alcohols. Doctoral thesis , UCL (University College London).

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Abstract

Propargylic alcohols are easily accessed through the reaction of alkynes with aldehydes and ketones. The 1,3-isomerisation of propargylic alcohols to enones is known as the Meyer-Schuster rearrangement. We have demonstrated efficient room temperature reaction conditions for the Au-catalysed Meyer-Schuster rearrangement (>30 examples) of a wide array of secondary and tertiary propargylic alcohols to the corresponding enones in generally excellent yields and with high E-selectivity. Primary propargylic alcohols rearrange to give highly reactive terminal enones, which can undergo conjugate addition reactions with nucleophiles to access β-substituted products through suitable one-pot procedures. Diethyl acetal substituted propargylic alcohols can be used to access synthetically useful 3-alkoxy furans in the presence of Au in high yield. The use of silver as a catalyst promotes substitution of the propargylic alcohol with various oxygen, carbon and nitrogen nucleophiles. β-Hydroxyketones can be accessed via a Au-catalysed hydration, employing phenols or acidic alcohols as the reaction additive.

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