Phosphine-Mediated Rauhut-Currier-Type/Acyl Transfer/ Wittig Strategy for Synthesis of Spirocyclopenta[c]chromene-Indolinones

Sandip Sambhaji Vagh, Bo Jhih Hou, Athukuri Edukondalu, Pin Ching Wang, 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

摘要

A phosphine-mediated reaction for the construction of spirocyclopenta[c]chromene-indolinones is reported via a Rauhut-Currier (RC)-type/acyl transfer/Wittig sequence. This methodology attributes the chemoselective phosphine addition to the alkynoate which generates the phosphorus zwitterion via RC-type reaction, and that further undergoes O-acylation to form the seven-membered betaine intermediate with acyl chloride in the presence of base. Extensive investigations reveal that the exceptional δ-acylation occurs through the C−O bond cleavage upon the seven-membered betaine, and the subsequent Wittig reaction preferentially result in the aforementioned spiro compounds. Furthermore, our protocol could also be applicable to different alkynoates to provide a series of spirocyclopenta[c]chromenones bearing privileged skeletons. (Figure presented.).

原文英語
頁(從 - 到)5429-5435
頁數7
期刊Advanced Synthesis and Catalysis
363
發行號24
DOIs
出版狀態已發佈 - 2021 12月 21

ASJC Scopus subject areas

  • 催化
  • 有機化學

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