Reactions of Sulfonium Salts with 2,3-Dioxopyrrolidine Derivatives: A Concise Synthesis of Spirocyclopropane

Shuang Zhang; Xiu-Qin Hu; Zhu-Yin Wang; Peng-Fei Xu

doi:10.1055/s-0034-1380522

Synthesis, Inhaltsverzeichnis

Synthesis 2015; 47(17): 2529-2537
DOI: 10.1055/s-0034-1380522

special topic

Reactions of Sulfonium Salts with 2,3-Dioxopyrrolidine Derivatives: A Concise Synthesis of Spirocyclopropane

Shuang Zhang

^aState Key Laboratory of Applied Organic Chemistry, and College of Chemistry and Chemical Engineering, Lanzhou University, Lanzhou 730000, P. R. of China eMail: xupf@lzu.edu.cn

,

Xiu-Qin Hu

^aState Key Laboratory of Applied Organic Chemistry, and College of Chemistry and Chemical Engineering, Lanzhou University, Lanzhou 730000, P. R. of China eMail: xupf@lzu.edu.cn

,

Zhu-Yin Wang

^bCollege of Mechanics and Materials, Hohai University, Nanjing 210098, P. R. of China

,

Peng-Fei Xu*

^aState Key Laboratory of Applied Organic Chemistry, and College of Chemistry and Chemical Engineering, Lanzhou University, Lanzhou 730000, P. R. of China eMail: xupf@lzu.edu.cn

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Abstract

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Abstract

An efficient base-promoted spirocyclopropanation of 2,3-dioxopyrrolidine derivatives with sulfonium salts is described. This reaction enables a novel concise access to polysubstituted spirocyclopropane derivatives in good yields and with a trans/cis ratio of up to >20:1 under mild conditions.

Key words

spiro compounds - spirocyclopropane - sulfur ylides - sulfonium salt - 2,3-dioxopyrrolidine - heterocycles

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Referenzen

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