Enantioselective Construction of Spirooxindole-Fused Cyclopenta[c]chromen-4-ones Bearing Five Contiguous Stereocenters via a Stepwise (3+2) Cycloaddition

Sandip Sambhaji Vagh, Praneeth Karanam, Cheng Chieh Liao, Ting Han Lin, Yan Cheng Liou, Athukuri Edukondalu, Yi Ru Chen, Wenwei Lin*

*此作品的通信作者

研究成果: 雜誌貢獻期刊論文同行評審

5 引文 斯高帕斯(Scopus)

摘要

The bifunctional quinine-catalyzed stepwise (3+2) cycloaddition for the enantioselective construction of spirooxindole-fused cyclopenta[c]chromen-4-ones is developed. The reactions of 3-homoacylcoumarins and alkylidene oxindole electrophiles generate aforementioned spirooxindole-chromenone adducts bearing five contiguous stereocenters, of which one is the spiro all-carbon quaternary stereocenter in high yields (up to 99%) with excellent stereoselectivities (up to >20:1 dr and 99% ee). This methodology was investigated for three different alkylidene oxindole electrophiles and could also be practically demonstrated on a gram scale. Mechanistic investigations revealed that the (3+2) cycloaddition for the enantioselective synthesis of spirooxindole-fused cyclopenta[c]chromen-4-ones is proceeding via a stepwise reaction pathway. (Figure presented.).

原文英語
頁(從 - 到)1679-1685
頁數7
期刊Advanced Synthesis and Catalysis
362
發行號8
DOIs
出版狀態已發佈 - 2020 四月 17

ASJC Scopus subject areas

  • 催化
  • 有機化學

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