Nucleophilic cyclopropanation of arylideneimidazolones possessing a peripheral chiral center and the subsequent fractional crystallization of diastereomers allows access to the compounds with an enantiomerically uniform configuration of the spirocyclic donoracceptor cyclopropane fragment. They were used to study the mechanism of the cycloaddition reaction with aldehydes; it was demonstrated that stereochemical information from the cyclopropane fragment is lost during the reaction.
This is a preview of subscription content, log in via an institution to check access.
Similar content being viewed by others
References
Strained Hydrocarbons: Beyond the van’t Hoff and Le Bel Hypothesis; Dodziuk, H., Ed.; Wiley, 2009.
(a) Reissig, H.-U.; Zimmer, R. Chem. Rev. 2003, 103, 1151. (b) Schneider, T. F.; Kaschel, J.; Werz, D. B. Angew. Chem., Int. Ed. 2014, 53, 5504. (c) Craig, A. J.; Hawkins, B. C. Synthesis 2020, 27. (d) Singh, P.; Varshnaya, R. K.; Dey, R.; Banerjee, P. Adv. Synth. Catal. 2020, 362, 1447. (e) Ivanova, O. A.; Trushkov, I. V. Chem. Rec. 2019, 19, 2189. (f) Novikov, R. A.; Tomilov, Yu. V. Mendeleev Commun. 2015, 25, 1.
(a) Yu, M.; Pagenkopf, B. L. Org. Lett. 2003, 5, 5099. (b) Yu, M.; Pantos, G. D.; Sessler, J. L.; Pagenkopf, B. L. Org. Lett. 2004, 6, 1057.
(a) Pohlhaus, P. D.; Johnson, J. S. J. Org. Chem. 2005, 70, 1057. (b) Pohlhaus, P. D.; Johnson, J. S. J. Am. Chem. Soc. 2005, 127, 16014. (c) Parsons, A. T.; Johnson, J. S. J. Am. Chem. Soc. 2009, 131, 3122.
(a) Carson, C. A.; Kerr, M. A. J. Org. Chem. 2005, 70, 8242. (b) Kang, Y.-B.; Tang, Y.; Sun, X.-L. Org. Biomol. Chem. 2006, 4, 299. (c) Parsons, A. T.; Smith, A. G.; Neel, A. J.; Johnson, J. S. J. Am. Chem. Soc. 2010, 132, 9688. (d) Garve, L. K. B.; Kreft, A.; Jones, P. G.; Werz, D. B. J. Org. Chem. 2017, 82, 9235.
(a) Ivanova, O. A.; Budynina, E. M.; Grishin, Y. K.; Trushkov, I. V.; Verteletskii, P. V. Angew. Chem., Int. Ed. 2008, 47, 1107. (b) Borisov, D. D.; Novikov, R. A.; Tomilov, Yu. V. Angew. Chem., Int. Ed. 2016, 55, 12233. (c) Chagarovskiy, A. O.; Vasin, V. S.; Kuznetsov, V. V.; Ivanova, O. A.; Rybakov, V. B.; Shumsky, A. N.; Makhova, N. N.; Trushkov, I. V. Angew. Chem., Int. Ed. 2018, 57, 10338. (d) Nambu, H.; Onuki, Y.; Ono, N.; Tsuge, K.; Yakura, T. Chem. Commun. 2019, 55, 6539. (e) Zhang, J.; Liao, Z.; Chen, L.; Jiang, H.; Zhu, S. Chem.–Eur. J. 2018, 24, 6927.
Mikhaylov, A. A.; Kuleshov, A. V.; Solyev, P. N.; Korlyukov, A. A.; Dorovatovskii, P. V.; Mineev, K. S.; Baranov, M. S. Org. Lett. 2020, 22, 2740.
(a) Tomilov, Yu. V.; Menchikov, L. G.; Novikov, R. A.; Ivanova, O. A.; Trushkov, I. V. Russ. Chem. Rev. 2018, 87, 201. [Usp. Khim. 2018, 87, 201.] (b) Ivanov, K. L.; Villemson, E. V.; Budynina, E. M.; Ivanova, O. A.; Trushkov, I. V.; Melnikov, M. Ya. Chem.–Eur. J. 2015, 21, 4975. a Cao, Z.-Y.; Zhou, F.; Yu, Y.-H.; Zhou, J. A. Org. Lett. 2013, 15, 42.
Rinaldi, P. L.; Naidu, M. S. R.; Conaway, W. E. J. Org. Chem. 1982, 47, 3987.
Schmidt, E. Ber. Dtsch. Chem. Ges. 1914, 47, 2545.
Dolomanov, O. V.; Bourhis, L. J.; Gildea, R. J.; Howard, J. A. K.; Puschman, H. J. Appl. Crystallogr. 2009, 42, 339.
Sheldrick, G. M. Acta Crystallogr., Sect. A: Found. Adv. 2015, A71, 3.
Sheldrick, G. M. Acta Crystallogr., Sect. C: Struct. Chem. 2015, C71, 3.
This work was supported by the Russian Science Foundation (grant 19-73-00319).
Author information
Authors and Affiliations
Corresponding authors
Additional information
Translated from Khimiya Geterotsiklicheskikh Soedinenii, 2020, 56(8), 1092–1096
Electronic supplementary material
ESM 1
(PDF 6540 kb)
Rights and permissions
About this article
Cite this article
Mikhaylov, A.А., Solyev, P.N., Kuleshov, A.V. et al. Imidazolone-activated donor-acceptor cyclopropanes with a peripheral stereocenter. A study on stereoselectivity of cycloaddition with aldehydes. Chem Heterocycl Comp 56, 1092–1096 (2020). https://doi.org/10.1007/s10593-020-02778-2
Received:
Accepted:
Published:
Issue Date:
DOI: https://doi.org/10.1007/s10593-020-02778-2