Open Access
Chimia, volume 63, issue 3, pages 162
Cyclization of Cyclopropyl Carbonyls and the Homo-Nazarov Reaction
Publication type: Journal Article
Publication date: 2009-03-25
General Chemistry
General Medicine
Abstract
Ring strain confers exceptional reactivity to the cyclopropane ring. Nevertheless, activation of the cyclopropane ring is usually needed to allow ring-opening reactions under mild conditions. The introduction of one or several carbonyl functionalities on cyclopropanes is often used to enhance their electrophilic reactivity. When a donor group is also present at the vicinal position to the carbonyl, more reactive donor–acceptor systems are obtained, which are ideally suited for homo-conjugate addition or cycloaddition reactions. This short review focuses on the special case of intramolecular cyclization reactions. Particular emphasis is devoted to the cyclization of vinyl- and aryl-cyclopropyl ketones for the formation of six-membered rings. This process corresponds to a formal homo-Nazarov cyclization and has been only used rarely in the past. Recently, the scope of the reaction was greatly expanded by the use of a silyl group as cation-stabilizing group and by the first catalytic method for the synthesis of vinyl-cyclopropyl ketones. With these new developments, the basis is now set for the application of this special class of cationic cyclizations to the synthesis of more complex synthetic and natural products.
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- We do not take into account publications without a DOI.
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De Simone F., Waser J. Cyclization of Cyclopropyl Carbonyls and the Homo-Nazarov Reaction // Chimia. 2009. Vol. 63. No. 3. p. 162.
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De Simone F., Waser J. Cyclization of Cyclopropyl Carbonyls and the Homo-Nazarov Reaction // Chimia. 2009. Vol. 63. No. 3. p. 162.
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TY - JOUR
DO - 10.2533/chimia.2009.162
UR - https://doi.org/10.2533/chimia.2009.162
TI - Cyclization of Cyclopropyl Carbonyls and the Homo-Nazarov Reaction
T2 - Chimia
AU - De, Simone
AU - Waser, J
PY - 2009
DA - 2009/03/25 00:00:00
PB - Schweizerische Chemische Gedellschaft
SP - 162
IS - 3
VL - 63
SN - 0009-4293
ER -
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@article{2009,
author = {Simone De and J Waser},
title = {Cyclization of Cyclopropyl Carbonyls and the Homo-Nazarov Reaction},
journal = {Chimia},
year = {2009},
volume = {63},
publisher = {Schweizerische Chemische Gedellschaft},
month = {mar},
url = {https://doi.org/10.2533/chimia.2009.162},
number = {3},
pages = {162},
doi = {10.2533/chimia.2009.162}
}