Gold-Catalyzed Cyclization of 2-Alkynylaldehyde Cyclic Acetals via Hydride Shift for the Synthesis of Indenone Derivatives

被引：19

作者：

Yamada, Tsuyoshi ^{[1
]}

Park, Kwihwan ^{[1
]}

Tachikawa, Takumu ^{[1
]}

Fujii, Akiko ^{[1
]}

Rudolph, Matthias ^{[2
]}

Hashmi, A. Stephen K. ^{[2
]}

Sajiki, Hironao ^{[1
]}

机构：

[1] Gifu Pharmaceut Univ, Lab Organ Chem, Gifu 5011196, Japan

[2] Heidelberg Univ, Organ Chem Inst, D-69120 Heidelberg, Germany

来源：

ORGANIC LETTERS | 2020年 / 22卷 / 05期

关键词：

CARBOALKOXYLATION; REARRANGEMENT; ALKYNES; CARBOCYCLES; ACTIVATION; CATIONS; ALLENES; KETONES; ETHERS; RING;

D O I：

10.1021/acs.orglett.0c00221

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

An efficient gold-catalyzed cyclization of 2-alkynylaldehyde cyclic acetals has been developed for the synthesis of indenone derivatives. A wide variety of functionalized indenone derivatives can be obtained in good-to-excellent yields. HMBC and NOESY NMR analyses and mechanistic elucidation experiments revealed that the cyclization occurs via a 1,5-H shift. The cyclic acetal group promoted the 1,5-H shift by activating the benzylic C-H bond and preventing the migration of the alkoxy group by tethering both alkoxy groups.

引用

页码：1883 / 1888

页数：6

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