高度非鏡像選擇性有機催化［2+2+2］環化反應合成全取代螺環吲哚酮

Highly Diastereoselective Synthesis of Fully Substituted Spirocyclic Oxindole via Organocatalysis [2+2+2] Annulation Reaction

林育賢(Lin Yu-Sian)

指導教授 ： 陳焜銘

國立臺灣師範大學/理學院/化學系/碩士(2022年)

https://doi.org/10.6345/NTNU202200966

摘要

此論文成功開發全取代螺環吲哚酮衍生物的合成方法，並且得到兩個四級碳中心，透過有機催化連鎖反應，進行 Michael/Michael/1,2-addition 反應。在 0 ℃的條件下，使用丙二腈、苄烯丙二腈、（E）-3-苄基-1-叔丁氧羰基-2-吲哚酮作為起始物，並以乙腈作為溶劑，加入催化量（30 mol%）的四甲基乙二胺，反應 8到 20 小時，製備全取代螺環吲哚酮衍生物，得到中等到良好的產率（45 - 81 %）、良好的非鏡像選擇性（14:1 - >20:1 d.r.）。

關鍵字

有機催化連鎖反應 ； 螺環吲哚酮

並列摘要

An efficient cascade protocol between malononitrile, benzylidenemalononitrile, and (E)-tert-butyl-3-benzylidene-2-oxoindoline-1-carboxylate has been developed. Fully substituted spirocyclic oxindole derivative bear two all-carbon quaternary centers. The reaction proceeds through a Michael/Michael/1,2-addition reaction. The spirocyclic oxindole derivatives were obtained in reasonable-to-good chemical yields (45 - 81 %) and high levels of diastereoselectivities (14:1 - >20:1 d.r.) using a catalytic amount of commercially available TMEDA (30 mol%) in ACN at 0 ℃ for 8 - 20 h.

並列關鍵字

cascade ； spirocyclic oxindoles

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