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 |
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頁(從 - 到) | 5429-5435 |
頁數 | 7 |
期刊 | Advanced Synthesis and Catalysis |
卷 | 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