SYNTHESIS OF <i>trans,trans</i>-2,3,4-TRISUBSTITUTED CHROMANES FROM 3-NITRO-2Н-CHROMENES AND ENAMINES OF ACETOACETIC ESTERAND ACETYLACETONE. A NEW TYPE OF CONFIGURATIONALLY STABLE ATROPISOMERS

Authors

  • Владислав Ю. Коротаев Institute of Natural Sciences, Ural Federal University named after the first President of Russia B. N. Yeltsin
  • Алексей Ю. Барков Institute of Natural Sciences, Ural Federal University named after the first President of Russia B. N. Yeltsin
  • Марина А. Ежикова I. Ya. Postovsky Institute of Organic Synthesis, Ural Branch of Russian Academy of Sciences
  • Михаил И. Кодесс I. Ya. Postovsky Institute of Organic Synthesis, Ural Branch of Russian Academy of Sciences
  • Вячеслав Я. Сосновских Institute of Natural Sciences, Ural Federal University named after the first President of Russia B. N. Yeltsin

DOI:

https://doi.org/10.1007/2460

Keywords:

3-nitro-2Н-chromenes, push-pull enamines, chromanes, atropisomerism, nucleophilic addition

Abstract

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 chromanes. The adducts obtaind from acetylacetone enamines represented mixtures of similar amounts of configurationally stable atropisomers, the formation of which was linked to hindered rotation around the C(sp3)–C(sp2) bond. A reaction with enamines of acetoacetic ester led practically exclusively to a single anti-atropisomer.

How to Cite
Korotaev, V. Yu.; Barkov, A. Yu.; Ezhikova, M. A.; Kodess, M. I.; Sosnovskikh, V. Ya. Chem. Heterocycl. Compd. 2015, 51, 531. [Khim. Geterotsikl. Soedin. 2015, 51, 531.]

For this article in the English edition see DOI 10.1007/s10593-015-1733-2

 

Author Biography

Вячеслав Я. Сосновских, Institute of Natural Sciences, Ural Federal University named after the first President of Russia B. N. Yeltsin

Вячеслав Яковлевич Сосновских

Зав. кафедрой органической химии Института естественных наук Уральского федерального университета

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Published

2015-07-06

Issue

Vol. 51 No. 6 (2015)

Section

Original Papers