Journal of the American Chemical Society, volume 143, issue 34, pages 13952-13961
Expanding Stereoelectronic Limits of endo-tet Cyclizations: Synthesis of Benz[b]azepines from Donor–Acceptor Cyclopropanes
Vartanova Anna E
1, 2
,
Plodukhin Andrey Yu
3
,
Ratmanova Nina K
4
,
Andreev Ivan A
1, 4
,
Anisimov Mikhail N
5, 6
,
Gudimchuk Nikita B.
5, 6
,
Levina Irina
7
,
Ivanova Olga
1, 3
,
Trushkov Igor V
1
,
3
5
6
7
Publication type: Journal Article
Publication date: 2021-08-18
Quartile SCImago
Q1
Quartile WOS
Q1
Impact factor: 15
ISSN: 00027863, 15205126
General Chemistry
Catalysis
Biochemistry
Colloid and Surface Chemistry
Abstract
The importance of intramolecular constraints in cyclic transition-state geometries is especially pronounced in n-endo-tet cyclizations, where the usual backside approach of a nucleophile to the breaking bond is impossible for the rings containing less than eight atoms. Herein, we expand the limits of endo-tet cyclizations and show that donor-acceptor cyclopropanes can provide a seven-membered ring via a genuine 6-endo-tet process. Substrates containing a N-alkyl-N-arylcarbamoyl moiety as an acceptor group undergo Lewis acid-induced cyclization to form tetrahydrobenz[b]azepin-2-ones in high yields. The reaction proceeds with the inversion of the configuration at the electrophilic carbon. In this process, a formally six-membered transition state yields a seven-membered ring as the pre-existing cycle is merged into the forming ring. The stereochemistry of the products can be controlled by the reaction time and by the nature of Lewis acid, opening access to both diastereomers by tuning of the reaction conditions.
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Citations by publishers
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4
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7
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7 publications, 29.17%
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1 publication, 4.17%
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1
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7
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- We do not take into account publications that without a DOI.
- Statistics recalculated only for publications connected to researchers, organizations and labs registered on the platform.
- Statistics recalculated weekly.
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Vartanova A. E. et al. Expanding Stereoelectronic Limits of endo-tet Cyclizations: Synthesis of Benz[b]azepines from Donor–Acceptor Cyclopropanes // Journal of the American Chemical Society. 2021. Vol. 143. No. 34. pp. 13952-13961.
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Vartanova A. E., Plodukhin A. Yu., Ratmanova N. K., Andreev I. A., Anisimov M. N., Gudimchuk N. B., Rybakov V. B., Levina I., Ivanova O., Trushkov I. V., Alabugin I. V. Expanding Stereoelectronic Limits of endo-tet Cyclizations: Synthesis of Benz[b]azepines from Donor–Acceptor Cyclopropanes // Journal of the American Chemical Society. 2021. Vol. 143. No. 34. pp. 13952-13961.
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TY - JOUR
DO - 10.1021/jacs.1c07088
UR - https://doi.org/10.1021%2Fjacs.1c07088
TI - Expanding Stereoelectronic Limits of endo-tet Cyclizations: Synthesis of Benz[b]azepines from Donor–Acceptor Cyclopropanes
T2 - Journal of the American Chemical Society
AU - Anisimov, Mikhail N
AU - Vartanova, Anna E
AU - Ratmanova, Nina K
AU - Andreev, Ivan A
AU - Ivanova, Olga
AU - Trushkov, Igor V
AU - Alabugin, Igor V.
AU - Plodukhin, Andrey Yu
AU - Gudimchuk, Nikita B.
AU - Rybakov, Victor B.
AU - Levina, Irina
PY - 2021
DA - 2021/08/18 00:00:00
PB - American Chemical Society (ACS)
SP - 13952-13961
IS - 34
VL - 143
SN - 0002-7863
SN - 1520-5126
ER -
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@article{2021_Vartanova,
author = {Mikhail N Anisimov and Anna E Vartanova and Nina K Ratmanova and Ivan A Andreev and Olga Ivanova and Igor V Trushkov and Igor V. Alabugin and Andrey Yu Plodukhin and Nikita B. Gudimchuk and Victor B. Rybakov and Irina Levina},
title = {Expanding Stereoelectronic Limits of endo-tet Cyclizations: Synthesis of Benz[b]azepines from Donor–Acceptor Cyclopropanes},
journal = {Journal of the American Chemical Society},
year = {2021},
volume = {143},
publisher = {American Chemical Society (ACS)},
month = {aug},
url = {https://doi.org/10.1021%2Fjacs.1c07088},
number = {34},
pages = {13952--13961},
doi = {10.1021/jacs.1c07088}
}
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Vartanova, Anna E., et al. “Expanding Stereoelectronic Limits of endo-tet Cyclizations: Synthesis of Benz[b]azepines from Donor–Acceptor Cyclopropanes.” Journal of the American Chemical Society, vol. 143, no. 34, Aug. 2021, pp. 13952-13961. https://doi.org/10.1021%2Fjacs.1c07088.