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

Tsuyoshi Yamada; Kwihwan Park; Takumu Tachikawa; Akiko Fujii; Matthias Rudolph; A. Stephen K. Hashmi; Hironao Sajiki

doi:10.1021/acs.orglett.0c00221

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

Tsuyoshi Yamada^*, Kwihwan Park, Takumu Tachikawa, Akiko Fujii, Matthias Rudolph, A. Stephen K. Hashmi, Hironao Sajiki

^*Corresponding author for this work

Synthetic and Medicinal Chemistry

Research output: Contribution to journal › Article › peer-review

24 Scopus citations

Abstract

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.

Original language	English
Pages (from-to)	1883-1888
Number of pages	6
Journal	Organic Letters
Volume	22
Issue number	5
DOIs	https://doi.org/10.1021/acs.orglett.0c00221
State	Published - 2020/03/06

ASJC Scopus subject areas

Biochemistry
Physical and Theoretical Chemistry
Organic Chemistry

Access to Document

10.1021/acs.orglett.0c00221

Cite this

@article{03ed8f23290843f8957979e5264f54af,

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

abstract = "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.",

author = "Tsuyoshi Yamada and Kwihwan Park and Takumu Tachikawa and Akiko Fujii and Matthias Rudolph and Hashmi, {A. Stephen K.} and Hironao Sajiki",

note = "Publisher Copyright: {\textcopyright} 2020 American Chemical Society.",

year = "2020",

month = mar,

day = "6",

doi = "10.1021/acs.orglett.0c00221",

language = "英語",

volume = "22",

pages = "1883--1888",

journal = "Organic Letters",

issn = "1523-7060",

publisher = "American Chemical Society",

number = "5",

}

TY - JOUR

T1 - Gold-Catalyzed Cyclization of 2-Alkynylaldehyde Cyclic Acetals via Hydride Shift for the Synthesis of Indenone Derivatives

AU - Yamada, Tsuyoshi

AU - Park, Kwihwan

AU - Tachikawa, Takumu

AU - Fujii, Akiko

AU - Rudolph, Matthias

AU - Hashmi, A. Stephen K.

AU - Sajiki, Hironao

PY - 2020/3/6

Y1 - 2020/3/6

N2 - 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.

AB - 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.

UR - http://www.scopus.com/inward/record.url?scp=85081944663&partnerID=8YFLogxK

U2 - 10.1021/acs.orglett.0c00221

DO - 10.1021/acs.orglett.0c00221

M3 - 学術論文

C2 - 32049540

AN - SCOPUS:85081944663

SN - 1523-7060

VL - 22

SP - 1883

EP - 1888

JO - Organic Letters

JF - Organic Letters

IS - 5

ER -

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

Abstract

ASJC Scopus subject areas

Access to Document

Fingerprint

Cite this