Enamines of acetoacetic ester and acetylacetone added at the activated double bond of 2-R1-3-nitro-2Н-chromenes (R1 = CF3, CCl3, Ph) with their central α-С atoms, forming trans,trans-2,3,4-trisubstituted chromans. The adducts obtained from acetylacetone enamines represented mixtures of comparable amounts of configurationally stable atropisomers, the formation of which was connected with hindered rotation around the C(sp 3)–C(sp 2) bond. A reaction with enamines of acetoacetic ester led practically exclusively to a single anti atropisomer.
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The results of this work were obtained within the framework of State Assignment by the Ministry of Education and Science of the Russian Federation with partial financial support from the Russian Foundation for Basic Research (project No. 14-03-00179).
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Translated from Khimiya Geterotsiklicheskikh Soedinenii, 2015, 51(6), 531–540
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Korotaev, V.Y., Barkov, A.Y., Ezhikova, M.A. et al. Synthesis of trans,trans-2,3,4-trisubstituted chromans from 3-nitro-2Н-chromenes and enamines of acetoacetic ester and acetylacetone. A new type of configurationally stable atropisomers. Chem Heterocycl Comp 51, 531–540 (2015). https://doi.org/10.1007/s10593-015-1733-2
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DOI: https://doi.org/10.1007/s10593-015-1733-2