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

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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 languageEnglish
Pages (from-to)3721-3724
Number of pages4
JournalChemistry - A European Journal
Volume24
Issue number15
DOIs
Publication statusPublished - 2018 Mar 12

Fingerprint

Gold
Phenols
Hydrogenation
Ligands
Derivatives
Air
Water
carbene
gabapentin

Keywords

  • carbenes
  • dearomatization
  • gold
  • spirocyclohexadienones
  • water

ASJC Scopus subject areas

  • Chemistry(all)

Cite this

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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, {Stephen Kyalo} and Takanori Shibata",
year = "2018",
month = "3",
day = "12",
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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, Stephen Kyalo

AU - Shibata, Takanori

PY - 2018/3/12

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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

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KW - gold

KW - spirocyclohexadienones

KW - water

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