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

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

doi:10.2174/157017806778700079

ISSN: 1570-1786
E-ISSN: 1875-6255

Alder-Ene Reaction of 3-Methyl-3-Cyanocyclopropene with Monoterpenes
Authors: Roman V. Ashirov¹, Alsu A. Balandina², Sergey V. Kharlamov³, Svetlana A. Appolonova⁴, Bruno Figadere⁵, Shamil K. Latypov⁶ and Vitali V. Plemenkov⁷
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¹ Institute of Organic and Physical Chemistry at the Kazan Scientific Centre, Russian Academy of Sciences, Arbuzov St., 8, Kazan 420088, Russia. ² Institute of Organic and Physical Chemistry at the Kazan Scientific Centre, Russian Academy of Sciences, Arbuzov St., 8, Kazan 420088, Russia. ³ Institute of Organic and Physical Chemistry at the Kazan Scientific Centre, Russian Academy of Sciences, Arbuzov St., 8, Kazan 420088, Russia. ⁴ Institute of Organic and Physical Chemistry at the Kazan Scientific Centre, Russian Academy of Sciences, Arbuzov St., 8, Kazan 420088, Russia. ⁵ Institute of Organic and Physical Chemistry at the Kazan Scientific Centre, Russian Academy of Sciences, Arbuzov St., 8, Kazan 420088, Russia. ⁶ Institute of Organic and Physical Chemistry at the Kazan Scientific Centre, Russian Academy of Sciences, Arbuzov St., 8, Kazan 420088, Russia. ⁷ Institute of Organic and Physical Chemistry at the Kazan Scientific Centre, Russian Academy of Sciences, Arbuzov St., 8, Kazan 420088, Russia.
Source: Letters in Organic Chemistry, Volume 3, Issue 9, Sep 2006, p. 670 - 673
DOI: https://doi.org/10.2174/157017806778700079
- Available online: 01 Sep 2006

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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2006-09-01

2025-09-16

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Article Type: Research Article

Keyword(s): Alder-ene reaction; NMR; stereochemistry

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

Abstract

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