Journal
ORGANIC LETTERS
Volume 23, Issue 8, Pages 3094-3099Publisher
AMER CHEMICAL SOC
DOI: 10.1021/acs.orglett.1c00780
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Funding
- National Natural Science Foundation of China [21702189, 21672193, 21272218]
- Key scientific and technological project of Henan Province [202102310004]
- China Ministry of industry and information technology [Z135060009002]
- China Postdoctoral Science Foundation [2017M610458, 2018T110737]
- Zhengzhou University of China
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A novel phosphine-catalyzed (4 + 2) cyclization reaction has been reported for the generation of functionalized dihydropyran skeletons from electron-deficient conjugated dienes and enones. Mechanistic investigation reveals the formation of a new phosphonium zwitterion, which undergoes consecutive reactions. An asymmetric variant has also been developed through efficient and economical chiral phosphine catalysis.
Herein we reported a novel phosphine-catalyzed (4 + 2) cyclization reaction of electron-deficient conjugated dienes with enones to generate functionalized dihydropyran skeletons. A mechanistic investigation reveals that the reaction produces a new phosphonium zwitterion, which undergoes consecutive reactions. In addition, an asymmetric variant was developed by efficient and economical chiral phosphine catalysis.
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