Enantioselective (8+3) Cycloadditions by Activation of Donor–Acceptor Cyclopropanes Employing Chiral Brønsted Base Catalysis
Publication type: Journal Article
Publication date: 2022-05-31
scimago Q1
wos Q1
SJR: 5.550
CiteScore: 27.6
Impact factor: 16.9
ISSN: 14337851, 15213773
PubMed ID:
35580010
General Chemistry
Catalysis
Abstract
A novel enantioselective (8+3) cycloaddition between donor-acceptor cyclopropanes and heptafulvenoids catalysed by a chiral bifunctional Brønsted base is described. Importantly, the reaction, which leverages an anionic activation strategy, is divergent from prototypical Lewis-acid activation protocols. A series of cyclopropylketones react with tropones affording the desired (8+3) cycloadducts in high yield and enantiomeric excess. For barbiturate substituted heptafulvenes, the (8+3) cycloaddition with cyclopropylketones proceeds in good yield, excellent diastereoselectivity and high enantiomeric excess. The experimental work is supported by DFT calculations, which indicate that the bifunctional organocatalyst activates both the donor-acceptor cyclopropane and tropone; the reaction proceeds in a step-wise manner with the ring-closure being the stereodetermining step
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31
Total citations:
31
Citations from 2024:
20
(64%)
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Mcleod D. et al. Enantioselective (8+3) Cycloadditions by Activation of Donor–Acceptor Cyclopropanes Employing Chiral Brønsted Base Catalysis // Angewandte Chemie - International Edition. 2022. Vol. 61. No. 29.
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Mcleod D., Thøgersen M. K., Barløse C. L., Skipper M. L., Obregón E. B., Kaasen Jørgensen K. Enantioselective (8+3) Cycloadditions by Activation of Donor–Acceptor Cyclopropanes Employing Chiral Brønsted Base Catalysis // Angewandte Chemie - International Edition. 2022. Vol. 61. No. 29.
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TY - JOUR
DO - 10.1002/anie.202206096
UR - https://doi.org/10.1002/anie.202206096
TI - Enantioselective (8+3) Cycloadditions by Activation of Donor–Acceptor Cyclopropanes Employing Chiral Brønsted Base Catalysis
T2 - Angewandte Chemie - International Edition
AU - Mcleod, David
AU - Thøgersen, Mathias Kirk
AU - Barløse, Casper Larsen
AU - Skipper, Mette Louise
AU - Obregón, Erlaitz Basabe
AU - Kaasen Jørgensen, K.
PY - 2022
DA - 2022/05/31
PB - Wiley
IS - 29
VL - 61
PMID - 35580010
SN - 1433-7851
SN - 1521-3773
ER -
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@article{2022_Mcleod,
author = {David Mcleod and Mathias Kirk Thøgersen and Casper Larsen Barløse and Mette Louise Skipper and Erlaitz Basabe Obregón and K. Kaasen Jørgensen},
title = {Enantioselective (8+3) Cycloadditions by Activation of Donor–Acceptor Cyclopropanes Employing Chiral Brønsted Base Catalysis},
journal = {Angewandte Chemie - International Edition},
year = {2022},
volume = {61},
publisher = {Wiley},
month = {may},
url = {https://doi.org/10.1002/anie.202206096},
number = {29},
doi = {10.1002/anie.202206096}
}