Two Faces of Styrylsulfonium Salts: Domino Michael Addition/Cyclopropanation of 2-(2-Acylvinyl)indoles for the Synthesis of Cyclopropa[3,4]pyrrolo[1,2-a]indoles

Two Faces of Styrylsulfonium Salts: Domino Michael Addition/Cyclopropanation of 2-(2-Acylvinyl)indoles for the Synthesis of Cyclopropa[3,4]pyrrolo[1,2-a]indoles Full article

Journal

Journal of Organic Chemistry
ISSN: 1520-6904 , E-ISSN: 0022-3263

Output data

Year: 2025, Volume: 90, Number: 7, Pages: 2682–2687 Pages count : DOI: 10.1021/acs.joc.4c02788

Authors

Fedorov Alexander A. ¹ , Myasnikov Danil A. ¹ , Mendogralo Elena Y. ¹ , Trushkov Igor V. ² , Uchuskin Maxim G. ¹

Affiliations

1	Perm State University, Bukireva st. 15, Perm 614990, Russian Federation
2	N.D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, Leninsky pr. 47, Moscow 119991, Russian Federation

We report a domino reaction of 2-(2-acylvinyl)indoles as well as the corresponding pyrroles with styrylsulfonium salts under mild conditions, affording cyclopropamitosene analogues in high yields and complete diastereoselectivity. A wide range of (E)-β-hetaryl-α,β-unsaturated ketones were successfully employed for the synthesis of potentially bioactive cyclopropa[3,4]pyrrolo[1,2-a]indoles and related cyclopropa[a]pyrrolizines, demonstrating the versatility of the developed method. In contrast, (Z)-isomers of the substrates fail to give cyclopropamitosene derivatives but undergo cyclopropanation of the terminal methyl group.

Fedorov A.A. , Myasnikov D.A. , Mendogralo E.Y. , Trushkov I.V. , Uchuskin M.G.
Two Faces of Styrylsulfonium Salts: Domino Michael Addition/Cyclopropanation of 2-(2-Acylvinyl)indoles for the Synthesis of Cyclopropa[3,4]pyrrolo[1,2-a]indoles
Journal of Organic Chemistry. 2025. V.90. N7. P.2682–2687. DOI: 10.1021/acs.joc.4c02788 WOS OpenAlex

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