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Asymmetric Diels-Alder reactions of cyclopentadiene in the synthesis of chiral norbornene derivatives

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Abstract

The review discusses available data on asymmetric Diels-Alder reactions of cyclopentadiene, which were published in the past decade. Both noncatalytic and catalytic (in the presence of achiral and chiral catalysts) versions of these reactions are considered. Effects of various factors on the chemical and optical yields, stereoselectivity, and optical purity of the Diels-Alder adducts are analyzed. Prospects in the development of this field of organic chemistry are examined.

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Authors and Affiliations

  1. Institute of Petrochemical Processes, National Academy of Sciences of Azerbaidjan, Khodzhalinskii pr. 30, Baku, 1025, Azerbaidjan

    E. G. Mamedov

  2. Zelinskii Institute of Organic Chemistry, Russian Academy of Sciences, Leninskii pr. 47, Moscow, 119991, Russia

    E. I. Klabunovskii

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Original Russian Text © E.G. Mamedov, E.I. Klabunovskii, 2008, published in Zhurnal Organicheskoi Khimii, 2008, Vol. 44, No. 8, pp. 1113–1135.

Mamedov El’dar Guseinkulu ogly was born in 1942 in the Kedabek Region, Azerbaidjan SSR. In 1965 he graduated from the Faculty of Pharmaceutics, Azerbaidjan State Medical Institute. E.G. Mamedov is Doctor of chemical sciences, Senior Research Worker at the Institute of Petrochemical Processes, National Academy of Sciences of Azerbaidjan.

Fields of scientific interest: functionally substituted alicyclic compounds, asymmetric syntheses, Diels-Alder reactions, physiologically active compounds.

Klabunovskii Evgenii Ivanovich was born in 1923 in Putivl’ (Ukrainian SSR). In 1944 he graduated from the Faculty of Chemistry, Moscow State Universitety. E.I. Klabunovskii is Doctor of chemical sciences, Professor, Honored Scientific Worker of the Russian Federation, Senior Research Worker at the Laboratory of Asymmetric Catalysis, Zelinskii Institute of Organic Chemistry, Russian Academy of Sciences.

Fields of scientific interest: homogeneous and heterogeneous asymmetric catalysis, natural origin of homochirality.

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Mamedov, E.G., Klabunovskii, E.I. Asymmetric Diels-Alder reactions of cyclopentadiene in the synthesis of chiral norbornene derivatives. Russ J Org Chem 44, 1097–1120 (2008). https://doi.org/10.1134/S1070428008080010

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