• Media type: E-Article
  • Title: Effective [3+1+1+1] Cycloaddition to Six‐Membered Carbocycle Based on DMSO as Dual Carbon Synthon
  • Contributor: Li, Hui; Su, Miaodong; Nie, Zhiwen; Yang, Tonglin; Luo, Weiping; Liu, Qiang; Guo, Cancheng
  • imprint: Wiley, 2021
  • Published in: Advanced Synthesis & Catalysis
  • Language: English
  • DOI: 10.1002/adsc.202100115
  • ISSN: 1615-4150; 1615-4169
  • Keywords: General Chemistry
  • Origination:
  • Footnote:
  • Description: <jats:title>Abstract</jats:title><jats:p>A [3+1+1+1] cycloaddition was developed among 2‐arylpropene, ketone and DMSO in the presence of K<jats:sub>2</jats:sub>S<jats:sub>2</jats:sub>O<jats:sub>8</jats:sub>. 2‐arylpropene provides three carbons, ketone offers one carbon, and DMSO as dual carbon donor contributes two carbons to the six‐membered carbocycle. It gave the cyclohexene motif and spirocyclohexene skeleton. Four C−C bonds formed in this process. Both propylene and ketone could be well tolerated and give the corresponding cyclohexene or spirocyclohexene motif in useful yields. Based on the controlled experiments, a possible mechanism was proposed.</jats:p><jats:p><jats:boxed-text content-type="graphic" position="anchor"><jats:graphic xmlns:xlink="http://www.w3.org/1999/xlink" mimetype="image/png" position="anchor" specific-use="enlarged-web-image" xlink:href="graphic/adsc202100115-toc-0001-m.png"><jats:alt-text>magnified image</jats:alt-text></jats:graphic></jats:boxed-text> </jats:p>