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
指紋
深入研究「Phosphine-Mediated Rauhut-Currier-Type/Acyl Transfer/ Wittig Strategy for Synthesis of Spirocyclopenta[c]chromene-Indolinones」主題。共同形成了獨特的指紋。資料集
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CCDC 2054089: Experimental Crystal Structure Determination
Sambhaji Vagh, S. (Contributor), Hou, B. (Contributor), Edukondalu, A. (Contributor), Wang, P. (Contributor), Chen, Y. (Contributor) & Lin, W. (Contributor), Cambridge Crystallographic Data Centre, 2022
DOI: 10.5517/ccdc.csd.cc26yfyk, http://www.ccdc.cam.ac.uk/services/structure_request?id=doi:10.5517/ccdc.csd.cc26yfyk&sid=DataCite
資料集: Dataset
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CCDC 2073322: Experimental Crystal Structure Determination
Sambhaji Vagh, S. (Contributor), Hou, B. (Contributor), Edukondalu, A. (Contributor), Wang, P. (Contributor), Chen, Y. (Contributor) & Lin, W. (Contributor), Cambridge Crystallographic Data Centre, 2022
DOI: 10.5517/ccdc.csd.cc27lgcp, http://www.ccdc.cam.ac.uk/services/structure_request?id=doi:10.5517/ccdc.csd.cc27lgcp&sid=DataCite
資料集: Dataset
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CCDC 2054088: Experimental Crystal Structure Determination
Sambhaji Vagh, S. (Contributor), Hou, B. (Contributor), Edukondalu, A. (Contributor), Wang, P. (Contributor), Chen, Y. (Contributor) & Lin, W. (Contributor), Cambridge Crystallographic Data Centre, 2022
DOI: 10.5517/ccdc.csd.cc26yfxj, http://www.ccdc.cam.ac.uk/services/structure_request?id=doi:10.5517/ccdc.csd.cc26yfxj&sid=DataCite
資料集: Dataset