Highly stereoselective dearomative [3 + 2] cycloadditon of cyclic pyridinium ylides to access spiro-indolizidine scaffolds

Spiro-indolizidine scaffolds are attractive structural motifs in natural alkaloids and pharmaceuticals. Herein, we described a highly stereoselective dearomative [3 + 2] cycloaddition between cyclic pyridinium ylides and nitroolefins. A novel type of cyclic pyridinium salts, which bear an electron-w...

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Bibliographic Details
Published in:Organic chemistry frontiers an international journal of organic chemistry 2021-10, Vol.8 (20), p.5847-5851
Main Authors: Xiao-Long, He, Wang, Cheng, You-Wu, Wen, Yi-Bing, Zhao, Yang, Huan, Qian, Shan, Yang, Lingling, Wang, Zhouyu
Format: Article
Language:English
Subjects:
Cycloaddition
Organic chemistry
Pyridinium
Reaction time
Rings (mathematics)
Salts
Scaffolds
Stereoselectivity
Substrates
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Summary:Spiro-indolizidine scaffolds are attractive structural motifs in natural alkaloids and pharmaceuticals. Herein, we described a highly stereoselective dearomative [3 + 2] cycloaddition between cyclic pyridinium ylides and nitroolefins. A novel type of cyclic pyridinium salts, which bear an electron-withdrawing group on the pyridine ring, have been developed as the ylide precusors and successfully applied in this cyclization. This protocol features a series of advantages inculding broad substrate scope, mild conditions, short reaction time and high level of yield and stereoselectivity, thus providing a concise and efficient method for the construction of spiro-indolizidine scaffolds.
ISSN:2052-4110
2052-4110
DOI:10.1039/d1qo00886b