The reactivity of 4-hydroxy- and 4-silyloxy-1,5-allenynes with homogeneous gold(I) catalysts

Organic Letters
Michael Wegener, Stefan F Kirsch

Abstract

Two new gold(I)-catalyzed cascade reactions of 4-hydroxy- and 4-silyloxy-1,5-allenynes are disclosed, offering access to a variety of mono- and bicyclic, polyunsaturated carbonyl compounds. The diverse reactivity observed for the investigated allenyne system is controlled by the nature of the unsaturated substrate: Allenynes bearing a free hydroxyl group engage in what is likely an oxycyclization/allene-ene carbocyclization cascade, while their silylated analogues are converted through a carbocyclization/pinacol-type rearrangement process.

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Citations

Mar 10, 2016·Journal of the American Chemical Society·Seyedmorteza HosseyniXiaodong Shi
Feb 28, 2017·Inorganic Chemistry·Philipp BertoccoChristoph Kirsch
May 28, 2016·Chemical Communications : Chem Comm·Sravan K ThummanapelliXiaodong Shi

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