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Ruthenium-catalyzed intramolecular metathesis of dienes and its application in the synthesis of bridged and spiro azabicycles

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Yurii Nikolaevich Bubnov 1, 2
Yurii Nikolaevich Bubnov
1 A. N. Nesmeyanov Institute of Organoelement Compounds of the Russian Academy of Sciences, Moscow
2 N.D. Zelinskii Institute of Organic Chemistry, Russian Academy of Sciences
10.1070/RCR4478
Published 30 November 2014
Communication , Volume 84, Issue 7, 758-785
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Kuznetsov N. Y., Bubnov Y. N. Ruthenium-catalyzed intramolecular metathesis of dienes and its application in the synthesis of bridged and spiro azabicycles // Russian Chemical Reviews. 2015. Vol. 84. No. 7. pp. 758-785.
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Kuznetsov N. Y., Bubnov Y. N. Ruthenium-catalyzed intramolecular metathesis of dienes and its application in the synthesis of bridged and spiro azabicycles // Russian Chemical Reviews. 2015. Vol. 84. No. 7. pp. 758-785.
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TY - JOUR
DO - 10.1070/RCR4478
UR - https://rcr.colab.ws/publications/10.1070/RCR4478
TI - Ruthenium-catalyzed intramolecular metathesis of dienes and its application in the synthesis of bridged and spiro azabicycles
T2 - Russian Chemical Reviews
AU - Kuznetsov, Nikolai Yur'evich
AU - Bubnov, Yurii Nikolaevich
PY - 2015
DA - 2014/11/30
PB - ANO Editorial Board of the journal Uspekhi Khimii
SP - 758-785
IS - 7
VL - 84
ER -
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@article{2015_Kuznetsov,
author = {Nikolai Yur'evich Kuznetsov and Yurii Nikolaevich Bubnov},
title = {Ruthenium-catalyzed intramolecular metathesis of dienes and its application in the synthesis of bridged and spiro azabicycles},
journal = {Russian Chemical Reviews},
year = {2015},
volume = {84},
publisher = {ANO Editorial Board of the journal Uspekhi Khimii},
month = {Nov},
url = {https://rcr.colab.ws/publications/10.1070/RCR4478},
number = {7},
pages = {758--785},
doi = {10.1070/RCR4478}
}
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Kuznetsov, Nikolai Yur'evich, and Yurii Nikolaevich Bubnov. “Ruthenium-catalyzed intramolecular metathesis of dienes and its application in the synthesis of bridged and spiro azabicycles.” Russian Chemical Reviews, vol. 84, no. 7, Nov. 2015, pp. 758-785. https://rcr.colab.ws/publications/10.1070/RCR4478.
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Abstract

The review presents a~historical excursion into catalytic alkene metathesis, covering the problems of history of the discovery of this process, as well as investigations on the properties, structure and reactivity of the most popular ruthenium catalysts for metathesis, mechanism of their action and decomposition. The main part covers studies devoted to the syntheses of bridged azabicyclic and $1$-azaspirocyclic compounds comprising the intramolecular metathesis of dienes as the key step. The formation of a~bicyclic skeleton of a~series of natural bridged (cocaine, ferruginine, calystegines, and anatoxin-a) and spiro (pinnaic acids, halichlorine, hystrionicotoxin, and cephalotaxine) azabicycles, as well as their analogues and compounds with larger rings is demonstrated. The methods for the synthesis of diene precursors and the conditions for final assembling of the bicyclic compounds are considered in detail. The generalization of the literature data allows one to efficiently carry out the mentioned process taking into account the most important features.

The bibliography includes 129 references.

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