Organophosphane-Catalyzed Construction of Functionalized 2-Ylideneoxindoles via Direct β-Acylation

Wey Chyng Jeng, Po Chung Chien, Sandip Sambhaji Vagh, Athukuri Edukondalu, 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

We report an efficient method for the direct β-acylation of 2-ylideneoxindoles with acyl chlorides that is catalyzed by organophosphanes in the presence of base. A variety of functionalized 2-ylideneoxindoles were prepared in moderate to good yields under mild, metalfree conditions via a tandem phospha-Michael/O-acylation/intramolecular cyclization/rearrangement sequence. Mechanistic investigations revealed that C-O bond cleavage on a possible betaine intermediate is the key step for the installation of the keto-functionality at the β-position of 2-ylideneoxindoles in a highly stereospecific manner. The synthetic utility of this protocol could also be proven by a scale-up reaction and synthetic transformations of the products.

原文英語
頁(從 - 到)4409-4418
頁數10
期刊Synthesis (Germany)
53
發行號23
DOIs
出版狀態已發佈 - 2021 十二月 1

ASJC Scopus subject areas

  • 催化
  • 有機化學

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