Substrate Specific Silver(I)-Catalyzed Cycloisomerization of Diene Involving Alkyl Rearrangements: Syntheses of 1,2,5,6-Tetrahydrocuminic Acid, &lt;i&gt;p&lt;/i&gt;-Menth-3-en-7-ol, and &lt;i&gt;p&lt;/i&gt;-Menth-3-en-7-al

Inagaki, Fuyuhiko; Matsumoto, Mizuki; Hira, Shisen; Mukai, Chisato

doi:10.1248/cpb.c17-00433

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Silver Catalyst (Agsbf 6 )1

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Cited by 2 publications

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“…Although the Ag-catalyzed cyclizations with alkynes 18,19) have been developed, the reaction of a simple alkene moiety [20][21][22][23] is still limited. Recently, we found that the Agcatalyst (AgSbF 6 ) worked with alkenes for the cycloisomerization and deprotection reaction.…”

Section: Silver Catalyst (Agsbf 6 )mentioning

confidence: 99%

Construction of 2,2-Dimethyloxepane Frameworks from Ene-Diols Catalyzed by Metal Catalyst or Brønsted Acid via 7-Endo-Trig Cyclization

Murakami

Maeda

Inagaki

2021

CHEMICAL & PHARMACEUTICAL BULLETIN

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The synthesis of 2,2-dimethyloxepane frameworks based on the 7-endo-trig cyclization of ene-diol using a catalytic amount of metal catalysts (Au, Ag) or Brønsted acid (TfOH) has been developed. Also, the spirotype dioxabicyclic products were also derived from the diene-diols. For the condition using metal catalysts, the cyclization selectively reacted between the 1,1,3-trisubstituted alkenes and alcohols to form the 2,2-dimethyloxepane frameworks. On the other hand, the TfOH reacted with not only the 1,1,2-trisubstituted alkene, but also the 1-substituted and 1,2-disubstituted alkenes providing the corresponding cyclic ethers, which is quite different from the conditions of the metal catalysts.

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