Synthesis of Densely Substituted Spirocyclobutanes from Activated Alkenes and Sulfur Ylides

Synthesis of Densely Substituted Spirocyclobutanes from Activated Alkenes and Sulfur Ylides Full article

Journal

Organic Letters
ISSN: 1523-7060 , E-ISSN: 1523-7052

Output data

Year: 2026, Volume: 28, Number: 20, Pages: 6293-6298 Pages count : 6 DOI: 10.1021/acs.orglett.6c01386

Authors

Boichenko Maksim A. ¹ , Tikhonov Timur P. ¹ , Shorokhov Vitaly V. ² , Lebedev Danila S. ^1,3 , Gaiazov Ernal R. ¹ , Zhokhov Sergey S. ¹ , Tafeenko Victor A. ¹ , Ratmanova Nina K. ¹ , Trushkov Igor V. ² , Andreev Ivan A. ¹ , Ivanova Olga A. ¹

Affiliations

1	Department of Chemistry, M. V. Lomonosov Moscow State University, Leninskie gory 1-3, Moscow 119991, Russia
2	N. D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, Leninsky pr. 47, Moscow 119991, Russia
3	HSE University

We report the direct synthesis of densely substituted spiroannulated cyclobutanes from indane-1,3-dione-based activated alkenes or their analogs and sulfur ylides under mild, Lewis acid-free conditions. The transformation proceeds through a Corey–Chaykovsky cyclopropanation that furnishes highly strained donor–acceptor spirocyclopropanes, followed by their (3 + 1)-annulation with stabilized sulfonium ylides that can be conducted in a telescoped or one-pot fashion. Preliminary mechanistic studies allowed a better understanding of the origin of both the observed high reactivity and diastereoselectivity.

Boichenko M.A. , Tikhonov T.P. , Shorokhov V.V. , Lebedev D.S. , Gaiazov E.R. , Zhokhov S.S. , Tafeenko V.A. , Ratmanova N.K. , Trushkov I.V. , Andreev I.A. , Ivanova O.A.
Synthesis of Densely Substituted Spirocyclobutanes from Activated Alkenes and Sulfur Ylides
Organic Letters. 2026. V.28. N20. P.6293-6298. DOI: 10.1021/acs.orglett.6c01386 WOS Scopus OpenAlex

Submitted:	Mar 30, 2026
Published online:	May 22, 2026

≡ Web of science:	WOS:001760112300001
≡ Scopus:	2-s2.0-105039748922
≡ OpenAlex:	W7160488646