Angewandte Chemie - International Edition, volume 61, issue 36
(4+3) Annulation of Donor‐Acceptor Cyclopropanes and Azadienes: Highly Stereoselective Synthesis of Azepanones
Publication type: Journal Article
Publication date: 2022-07-28
Quartile SCImago
Q1
Quartile WOS
Q1
Impact factor: 16.6
ISSN: 14337851, 15213773
General Chemistry
Catalysis
Abstract
Azepanes are important seven-membered heterocycles, which are present in numerous natural and synthetic compounds. However, the development of convergent synthetic methods to access them remains challenging. Herein, we report the Lewis acid catalyzed (4+3) annulative addition of aryl and amino donor-acceptor cyclopropanes with 2-aza-1,3-dienes. Densely substituted azepane derivatives were obtained in good to excellent yields and with high diastereoselectivity. The reaction occurred under mild conditions with ytterbium triflate as the catalyst. The use of copper triflate with a trisoxazoline (Tox) ligand led to an enantioselective transformation. The obtained cycloadducts were convenient substrates for a series of further modifications, showing the synthetic utility of these compounds.
Top-30
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Citations by publishers
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7 publications, 33.33%
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- We do not take into account publications without a DOI.
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- Statistics recalculated weekly.
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Nicolai S., Waser J. (4+3) Annulation of Donor‐Acceptor Cyclopropanes and Azadienes: Highly Stereoselective Synthesis of Azepanones // Angewandte Chemie - International Edition. 2022. Vol. 61. No. 36.
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Nicolai S., Waser J. (4+3) Annulation of Donor‐Acceptor Cyclopropanes and Azadienes: Highly Stereoselective Synthesis of Azepanones // Angewandte Chemie - International Edition. 2022. Vol. 61. No. 36.
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TY - JOUR
DO - 10.1002/anie.202209006
UR - https://doi.org/10.1002/anie.202209006
TI - (4+3) Annulation of Donor‐Acceptor Cyclopropanes and Azadienes: Highly Stereoselective Synthesis of Azepanones
T2 - Angewandte Chemie - International Edition
AU - Nicolai, Stefano
AU - Waser, Jerome
PY - 2022
DA - 2022/07/28 00:00:00
PB - Wiley
IS - 36
VL - 61
SN - 1433-7851
SN - 1521-3773
ER -
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@article{2022_Nicolai,
author = {Stefano Nicolai and Jerome Waser},
title = {(4+3) Annulation of Donor‐Acceptor Cyclopropanes and Azadienes: Highly Stereoselective Synthesis of Azepanones},
journal = {Angewandte Chemie - International Edition},
year = {2022},
volume = {61},
publisher = {Wiley},
month = {jul},
url = {https://doi.org/10.1002/anie.202209006},
number = {36},
doi = {10.1002/anie.202209006}
}