Catalytic Dearomative Spirocyclization via Gold Carbene Species Derived from Ynamides: Efficient Synthesis of 2-Azaspiro[4.5]decan-3-ones

Mamoru Ito; Ryosuke Kawasaki; Kyalo Stephen Kanyiva; Takanori Shibata

doi:10.1002/chem.201800314

Catalytic Dearomative Spirocyclization via Gold Carbene Species Derived from Ynamides: Efficient Synthesis of 2-Azaspiro[4.5]decan-3-ones

Mamoru Ito, Ryosuke Kawasaki, Kyalo Stephen Kanyiva, Takanori Shibata^*

^*Corresponding author for this work

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

15 Citations (Scopus)

Abstract

An intramolecular catalytic dearomatization of phenols via gold carbene species proceeded to provide 2-azaspiro[4.5]decan-3-ones. The use of NHC ligand and water as a co-solvent was critical for achieving high reactivity. This reaction did not require hazardous diazo compounds as carbene sources and proceeded even under air. The obtained spirocyclic product could be readily transformed into a gabapentin derivative by hydrogenation and deprotection.

Original language	English
Pages (from-to)	3721-3724
Number of pages	4
Journal	Chemistry - A European Journal
Volume	24
Issue number	15
DOIs	https://doi.org/10.1002/chem.201800314
Publication status	Published - 2018 Mar 12

Keywords

carbenes
dearomatization
gold
spirocyclohexadienones
water

ASJC Scopus subject areas

Catalysis
Organic Chemistry

Access to Document

10.1002/chem.201800314

Cite this

@article{2e1d96b96e9d41e29d0dfb8014493821,

title = "Catalytic Dearomative Spirocyclization via Gold Carbene Species Derived from Ynamides: Efficient Synthesis of 2-Azaspiro[4.5]decan-3-ones",

abstract = "An intramolecular catalytic dearomatization of phenols via gold carbene species proceeded to provide 2-azaspiro[4.5]decan-3-ones. The use of NHC ligand and water as a co-solvent was critical for achieving high reactivity. This reaction did not require hazardous diazo compounds as carbene sources and proceeded even under air. The obtained spirocyclic product could be readily transformed into a gabapentin derivative by hydrogenation and deprotection.",

keywords = "carbenes, dearomatization, gold, spirocyclohexadienones, water",

author = "Mamoru Ito and Ryosuke Kawasaki and Kanyiva, {Kyalo Stephen} and Takanori Shibata",

note = "Funding Information: This work was supported by JST, ACT-C, Japan and Waseda University Grant for Special Research Projects. M.I. is grateful to generous support from “Early Bird” grant for young researcher at Waseda Research Institute for Science and Engineering. Publisher Copyright: {\textcopyright} 2018 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim",

year = "2018",

month = mar,

day = "12",

doi = "10.1002/chem.201800314",

language = "English",

volume = "24",

pages = "3721--3724",

journal = "Chemistry - A European Journal",

issn = "0947-6539",

publisher = "Wiley-VCH Verlag",

number = "15",

}

TY - JOUR

T1 - Catalytic Dearomative Spirocyclization via Gold Carbene Species Derived from Ynamides

T2 - Efficient Synthesis of 2-Azaspiro[4.5]decan-3-ones

AU - Ito, Mamoru

AU - Kawasaki, Ryosuke

AU - Kanyiva, Kyalo Stephen

AU - Shibata, Takanori

N1 - Funding Information: This work was supported by JST, ACT-C, Japan and Waseda University Grant for Special Research Projects. M.I. is grateful to generous support from “Early Bird” grant for young researcher at Waseda Research Institute for Science and Engineering. Publisher Copyright: © 2018 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim

PY - 2018/3/12

Y1 - 2018/3/12

N2 - An intramolecular catalytic dearomatization of phenols via gold carbene species proceeded to provide 2-azaspiro[4.5]decan-3-ones. The use of NHC ligand and water as a co-solvent was critical for achieving high reactivity. This reaction did not require hazardous diazo compounds as carbene sources and proceeded even under air. The obtained spirocyclic product could be readily transformed into a gabapentin derivative by hydrogenation and deprotection.

AB - An intramolecular catalytic dearomatization of phenols via gold carbene species proceeded to provide 2-azaspiro[4.5]decan-3-ones. The use of NHC ligand and water as a co-solvent was critical for achieving high reactivity. This reaction did not require hazardous diazo compounds as carbene sources and proceeded even under air. The obtained spirocyclic product could be readily transformed into a gabapentin derivative by hydrogenation and deprotection.

KW - carbenes

KW - dearomatization

KW - gold

KW - spirocyclohexadienones

KW - water

UR - http://www.scopus.com/inward/record.url?scp=85042160142&partnerID=8YFLogxK

UR - http://www.scopus.com/inward/citedby.url?scp=85042160142&partnerID=8YFLogxK

U2 - 10.1002/chem.201800314

DO - 10.1002/chem.201800314

M3 - Article

C2 - 29372752

AN - SCOPUS:85042160142

SN - 0947-6539

VL - 24

SP - 3721

EP - 3724

JO - Chemistry - A European Journal

JF - Chemistry - A European Journal

IS - 15

ER -

Catalytic Dearomative Spirocyclization via Gold Carbene Species Derived from Ynamides: Efficient Synthesis of 2-Azaspiro[4.5]decan-3-ones

Abstract

Keywords

ASJC Scopus subject areas

Access to Document

Other files and links

Fingerprint

Cite this