Asymmetric induction in thia-Diels-Alder reactions of chiral polyfluoroalkylthionocarboxylates

Timoshenko VM, Siry SA, Rozhenko AB, Shermolovich YG (2010)
JOURNAL OF FLUORINE CHEMISTRY 131(2): 172-183.

Zeitschriftenaufsatz | Veröffentlicht | Englisch
 
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Autor/in
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Abstract / Bemerkung
A series of chiral S- or O-alkyl thionoesters have been synthesized by treatment of trifluorothioacetyl- or 2,2,3,3-tetrafluorothiopropionyl chloride with corresponding thiols or alcohols. The thia-Diels-Alder reaction of the thionoesters with symmetrical 1,3-dienes proceeds with diastereoselectivity up to 60%. Structures of cycloaddition products and corresponding transition states have been studied at the DFT level of approximation. The experimentally observed diastereomeric excess has been referred to differences in activation energies of transition states, preceding formation of the diastereomeric cycloaducts. (C) 2009 Elsevier B.V. All rights reserved.
Stichworte
DFT; Asymmetric induction; Dihydrothiopyrans; Thia-Diels-Alder reaction; Fluorine; Thioesters; Transition state
Erscheinungsjahr
2010
Zeitschriftentitel
JOURNAL OF FLUORINE CHEMISTRY
Band
131
Ausgabe
2
Seite(n)
172-183
ISSN
0022-1139
Page URI
https://pub.uni-bielefeld.de/record/1796593

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Timoshenko VM, Siry SA, Rozhenko AB, Shermolovich YG. Asymmetric induction in thia-Diels-Alder reactions of chiral polyfluoroalkylthionocarboxylates. JOURNAL OF FLUORINE CHEMISTRY. 2010;131(2):172-183.
Timoshenko, V. M., Siry, S. A., Rozhenko, A. B., & Shermolovich, Y. G. (2010). Asymmetric induction in thia-Diels-Alder reactions of chiral polyfluoroalkylthionocarboxylates. JOURNAL OF FLUORINE CHEMISTRY, 131(2), 172-183. doi:10.1016/j.jfluchem.2009.11.011
Timoshenko, V. M., Siry, S. A., Rozhenko, A. B., and Shermolovich, Y. G. (2010). Asymmetric induction in thia-Diels-Alder reactions of chiral polyfluoroalkylthionocarboxylates. JOURNAL OF FLUORINE CHEMISTRY 131, 172-183.
Timoshenko, V.M., et al., 2010. Asymmetric induction in thia-Diels-Alder reactions of chiral polyfluoroalkylthionocarboxylates. JOURNAL OF FLUORINE CHEMISTRY, 131(2), p 172-183.
V.M. Timoshenko, et al., “Asymmetric induction in thia-Diels-Alder reactions of chiral polyfluoroalkylthionocarboxylates”, JOURNAL OF FLUORINE CHEMISTRY, vol. 131, 2010, pp. 172-183.
Timoshenko, V.M., Siry, S.A., Rozhenko, A.B., Shermolovich, Y.G.: Asymmetric induction in thia-Diels-Alder reactions of chiral polyfluoroalkylthionocarboxylates. JOURNAL OF FLUORINE CHEMISTRY. 131, 172-183 (2010).
Timoshenko, Vadim M., Siry, Sergiy A., Rozhenko, Alexander B., and Shermolovich, Yuriy G. “Asymmetric induction in thia-Diels-Alder reactions of chiral polyfluoroalkylthionocarboxylates”. JOURNAL OF FLUORINE CHEMISTRY 131.2 (2010): 172-183.