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Controlling the Gold(I)-Catalyzed 1,5-Allenene Reaction: Construction of Fused Rings with Excellent Diastereoselectivity.

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In the present study, the gold(I)-catalyzed reaction of 1,5-allenenes was controlled in such a way that instead of a [2 + 3] cycloaddition, a 5-exo-cyclization with the formation of a… Click to show full abstract

In the present study, the gold(I)-catalyzed reaction of 1,5-allenenes was controlled in such a way that instead of a [2 + 3] cycloaddition, a 5-exo-cyclization with the formation of a carbocation occurred. The latter could be trapped with both oxygen and carbon nucleophiles. In the investigated system, fused tricyclic frameworks with three contiguous stereocenters with excellent chemo- and diastereoselectivity in up to 95% yield were obtained.

Keywords: diastereoselectivity; controlling gold; catalyzed allenene; reaction; gold; gold catalyzed

Journal Title: Organic letters
Year Published: 2021

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