Participation of β‑Ketothioamides in N‑Heterocyclic Carbene- Catalyzed [3 + 3] Spiroannulation: Asymmetric Synthesis of Functionalized Spiro-piperidinone Derivatives
Participation of β‑Ketothioamides in N‑Heterocyclic Carbene- Catalyzed [3 + 3] Spiroannulation: Asymmetric Synthesis of Functionalized Spiro-piperidinone Derivatives
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β-酮硫酰胺参与 N-杂环卡宾催化 [3 3] 螺环化：功能化螺哌啶酮衍生物的不对称合成
DOI：
10.1021/acs.joc.8b02520
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发表时间：
2018
期刊：
影响因子：
--
通讯作者：
Peng-Fei Xu
中科院分区：
文献类型：
--
作者：
Hong Lu;Chang-Yin Tan;Huan-Xin Zhang;Jia-Lu Zhang;Jin-Yu Liu;Hong-Yu Li;Peng-Fei Xu
本文报道了一种N-杂环卡宾催化的β-酮硫代酰胺的不对称[3 + 3]螺环化反应。β-硫代酮酰胺具有独特的内酰胺化反应活性，以高产率、高立体选择性合成了含有两个邻位立体异构中心的螺环哌啶酮衍生物，其结构可以顺利转化为相应的酰亚胺和δ-内酰胺衍生物。
An N-heterocyclic carbene-catalyzed asymmetric [3 + 3] spiroannulation of β-ketothioamide was successfully developed. β-Ketothioamides exhibit an unusual reactivity to undergo a previously challenging lactamization reaction, and the desired spiro-piperidinone derivatives containing two vicinal stereogenic centers were synthesized in good to high yields with high stereoselectivities, whose structure can be converted to the corresponding imide and δ-lactam derivatives smoothly.