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Methods for the synthesis of donor-acceptor cyclopropanes

, 
Leonid Gennad'evich Menchikov 1
Leonid Gennad'evich Menchikov
, 
Roman Aleksandrovich Novikov 1
Roman Aleksandrovich Novikov
,  , 
Igor Viktorovich Trushkov 3
Igor Viktorovich Trushkov
1 N.D. Zelinskii Institute of Organic Chemistry, Russian Academy of Sciences
2 Lomonosov Moscow State University, Faculty of Chemistry
3 Peoples Friendship University of Russia, Moscow
Published 30 November 2017
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Tomilov Y. V. et al. Methods for the synthesis of donor-acceptor cyclopropanes // Russian Chemical Reviews. 2017. Vol. 87. No. 3. pp. 201-250.
GOST all authors (up to 50)
Tomilov Y. V., Menchikov L. G., Novikov R. A., Ivanova O. A., Trushkov I. V. Methods for the synthesis of donor-acceptor cyclopropanes // Russian Chemical Reviews. 2017. Vol. 87. No. 3. pp. 201-250.
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TY - JOUR
DO - 10.1070/RCR4787
UR - https://rcr.colab.ws/publications/10.1070/RCR4787
TI - Methods for the synthesis of donor-acceptor cyclopropanes
T2 - Russian Chemical Reviews
AU - Tomilov, Yury Vasil'evich
AU - Menchikov, Leonid Gennad'evich
AU - Novikov, Roman Aleksandrovich
AU - Ivanova, Ol'ga Aleksandrovna
AU - Trushkov, Igor Viktorovich
PY - 2017
DA - 2017/11/30
PB - ANO Editorial Board of the journal Uspekhi Khimii
SP - 201-250
IS - 3
VL - 87
ER -
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@article{2017_Tomilov,
author = {Yury Vasil'evich Tomilov and Leonid Gennad'evich Menchikov and Roman Aleksandrovich Novikov and Ol'ga Aleksandrovna Ivanova and Igor Viktorovich Trushkov},
title = {Methods for the synthesis of donor-acceptor cyclopropanes},
journal = {Russian Chemical Reviews},
year = {2017},
volume = {87},
publisher = {ANO Editorial Board of the journal Uspekhi Khimii},
month = {Nov},
url = {https://rcr.colab.ws/publications/10.1070/RCR4787},
number = {3},
pages = {201--250},
doi = {10.1070/RCR4787}
}
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Cite this
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Tomilov, Yury Vasil'evich, et al. “Methods for the synthesis of donor-acceptor cyclopropanes.” Russian Chemical Reviews, vol. 87, no. 3, Nov. 2017, pp. 201-250. https://rcr.colab.ws/publications/10.1070/RCR4787.
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Abstract

The interest in cyclopropane derivatives is caused by the facts that, first, the three-carbon ring is present in quite a few natural and biologically active compounds and, second, compounds with this ring are convenient building blocks for the synthesis of diverse molecules (acyclic, alicyclic and heterocyclic). The carbon--carbon bonds in cyclopropane are kinetically rather inert; hence, they need to be activated to be involved in reactions. An efficient way of activation is to introduce vicinal electron-donating and electron-withdrawing substituents into the ring; these substrates are usually referred to as donor-acceptor cyclopropanes. This review gives a systematic account of the key methods for the synthesis of donor-acceptor cyclopropanes. The most important among them are reactions of nucleophilic alkenes with diazo compounds and iodonium ylides and approaches based on reactions of electrophilic alkenes with sulfur ylides (the Corey--Chaykovsky reaction). Among other methods used for this purpose, noteworthy are cycloalkylation of CH-acids, addition of $\alpha$-halocarbonyl compounds to alkenes, cyclization \textit{via} 1,3-elimination, reactions of alkenes with halocarbenes followed by reduction, the Simmons--Smith reaction and some other. The scope of applicability and prospects of various methods for the synthesis of donor-acceptor cyclopropanes are discussed.

The bibliography includes 530 references.

Funders

Russian Science Foundation
14-13-01054П
Ministry of Education and Science of the Russian Federation
НШ-8012.2016.3

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