通过由烯炔酰胺衍生的金卡宾物种实现的催化去芳构化螺环化反应：2-氮杂螺[4.5]癸-3-酮的高效合成
Catalytic Dearomative Spirocyclization via Gold Carbene Species Derived from Ynamides: Efficient Synthesis of 2-Azaspiro[4.5]decan-3-ones.
作者信息
Ito Mamoru, Kawasaki Ryosuke, Kanyiva Kyalo Stephen, Shibata Takanori
机构信息
Department of Chemistry and Biochemistry, School of Advanced Science and Engineering, Waseda University, Shinjuku, Tokyo, 169-8555, Japan.
Global Center for Science and Engineering, School of Advanced Science and Engineering, Waseda University, Shinjuku, Tokyo, 169-8555, Japan.
出版信息
Chemistry. 2018 Mar 12;24(15):3721-3724. doi: 10.1002/chem.201800314. Epub 2018 Feb 19.
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.
通过金卡宾物种实现的酚类分子内催化脱芳构化反应生成了2-氮杂螺[4.5]癸烷-3-酮。使用NHC配体和水作为共溶剂对于实现高反应活性至关重要。该反应不需要危险的重氮化合物作为卡宾源，甚至在空气中也能进行。所得到的螺环产物可以通过氢化和脱保护反应轻松转化为加巴喷丁衍生物。
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