Alder-Ene Reaction of 3-Methyl-3-Cyanocyclopropene with Monoterpenes

Roman   V.   Ashirov; Ruslan   V.   Ashirov; Alsu   A.   Balandina; Sergey   V.   Kharlamov; Svetlana   A.   Appolonova; Bruno      Figadere; Shamil   K.   Latypov; Vitali   V.   Plemenkov

doi:10.2174/157017806778700079

Abstract

Sesquiterpene adducts have been obtained by the reactions of 3-methyl-3-cyanocyclopropene with (-) -pinene and (-)carvone, proceeding by Alder-ene pathway. In the reaction with -pinene only one diastereoisomer (∼95 %) was formed, while in the case of carvone a mixture of two diastereoisomers almost in equal quantities (55:45) was obtained.

Keywords: Alder-ene reaction, NMR, stereochemistry

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Letters in Organic Chemistry

Title: Alder-Ene Reaction of 3-Methyl-3-Cyanocyclopropene with Monoterpenes

Volume: 3 Issue: 9

Author(s): Roman V. Ashirov, Ruslan V. Ashirov, Alsu A. Balandina, Sergey V. Kharlamov, Svetlana A. Appolonova, Bruno Figadere, Shamil K. Latypov and Vitali V. Plemenkov

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Keywords: Alder-ene reaction, NMR, stereochemistry

Abstract: Sesquiterpene adducts have been obtained by the reactions of 3-methyl-3-cyanocyclopropene with (-) -pinene and (-)carvone, proceeding by Alder-ene pathway. In the reaction with -pinene only one diastereoisomer (∼95 %) was formed, while in the case of carvone a mixture of two diastereoisomers almost in equal quantities (55:45) was obtained.

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Ashirov V. Roman, Ashirov V. Ruslan, Balandina A. Alsu, Kharlamov V. Sergey, Appolonova A. Svetlana, Figadere Bruno, Latypov K. Shamil and Plemenkov V. Vitali, Alder-Ene Reaction of 3-Methyl-3-Cyanocyclopropene with Monoterpenes, Letters in Organic Chemistry 2006; 3 (9) . https://dx.doi.org/10.2174/157017806778700079