Unprecedented chemoselective Ru(iii)-catalyzed [3 + 2] annulation of enaminones with iodonium ylides for the synthesis of functionalized 3a,7a-dihydroxy hexahydro-4H-indol-4-ones

Herein, a straightforward and efficient method to obtain 3a,7a-dihydroxy hexahydro-4H-indol-4-ones via Ru(iii)-catalyzed alkenyl C(sp2)–H bond functionalization/[3 + 2] annulation of enaminones with iodonium ylides has been described. This protocol features chemoselectivity, broad substrate scope, m...

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Published in:Organic chemistry frontiers an international journal of organic chemistry 2023-11, Vol.10 (22), p.5660-5666
Main Authors: Zhang, Mingshuai, Chen, Longkun, Liu, Zhuoyuan, Huang, Jiuzhong, Yu, Fuchao
Format: Article
Language:English
Subjects:
Chemical reactions
Chemical synthesis
Hydrogen bonds
Organic chemistry
Substrates
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Summary:Herein, a straightforward and efficient method to obtain 3a,7a-dihydroxy hexahydro-4H-indol-4-ones via Ru(iii)-catalyzed alkenyl C(sp2)–H bond functionalization/[3 + 2] annulation of enaminones with iodonium ylides has been described. This protocol features chemoselectivity, broad substrate scope, moderate to excellent yields, gram-scale synthesis, and mild reaction conditions. The newly formed 3a,7a-dihydroxy hexahydro-4H-indol-4-one scaffolds can be easily further derivatized to 1H-pyrrol-3-ol carboxylate derivatives through an open-ring/hydrolysis transformation, showing potential applications in organic synthesis and medicinal chemistry.
ISSN:2052-4110
2052-4110
DOI:10.1039/d3qo01276j