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

被引：20

作者：

Ito, Mamoru ^{[1
]}

Kawasaki, Ryosuke ^{[1
]}

Kanyiva, Kyalo Stephen ^{[2
]}

Shibata, Takanori ^{[1
,3
]}

机构：

[1] Waseda Univ, Sch Adv Sci & Engn, Dept Chem & Biochem, Shinjuku Ku, Tokyo 1698555, Japan

[2] Waseda Univ, Sch Adv Sci & Engn, Global Ctr Sci & Engn, Shinjuku Ku, Tokyo 1698555, Japan

[3] ACT C Japan Sci & Technol Agcy JST, 4-1-8 Honcho, Kawaguchi, Saitama 3320012, Japan

来源：

CHEMISTRY-A EUROPEAN JOURNAL | 2018年 / 24卷 / 15期

关键词：

carbenes; dearomatization; gold; spirocyclohexadienones; water; ASYMMETRIC DEAROMATIZATION; INTRAMOLECULAR DEAROMATIZATION; INTERMOLECULAR OXIDATION; DERIVATIVES; PHENOL; ALKYNES; ACCESS; SPIROCARBOCYCLES; DIAZOACETAMIDES; CONSTRUCTION;

D O I：

10.1002/chem.201800314

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

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.

引用

页码：3721 / 3724

页数：4

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