Gold(I)-catalysed tandem cyclization of propargyl acetals and alkynes

Add time:07/24/2019    Source:sciencedirect.com

To expand the understanding of the chemistry of propargyl acetals, their gold(I) catalysed cycloaddition reactions with alkynes have been investigated. We hereby report a novel tandem reaction that allows the construction of a new type of polysubstituted and highly functionalised bicyclic pentalene compounds, 2,6a-dimethoxy-3a-methyl-1,4,5-triphenyl-1,3a,4,6a-tetrahydropentalenes, with four stereogenic centres.Pure diastereomers were successfully isolated in up to 51% yield from mixtures of diastereomeric products (up to 60% total yield) and characterized individually by NMR spectroscopy. A plausible mechanism for the formation of these novel tandem products, based on subsequent [2+2] and [2+3] cycloadditions, is proposed for this gold(I) catalysed reaction.

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