GaCl3 catalyzed the cascade Michael/ketalization of o-hydroxychalcones with indoline-2-thiones: For the construction of indole-annulated 2-oxa-8-thiabicyclo[3.3.1]nonane derivatives
Publication type: Journal Article
Publication date: 2022-09-01
scimago Q3
wos Q3
SJR: 0.334
CiteScore: 3.2
Impact factor: 1.5
ISSN: 00404039, 18733581
Organic Chemistry
Drug Discovery
Biochemistry
Abstract
A GaCl 3 -catalyzed highly diastereoselective Michael addition/ketalization of o -hydroxychalcones with indoline-2-thiones has been realized, leading to biologically important indole-annulated 2-oxa-8-thiabicyclo[3.3.1]nonane derivatives in moderate to excellent yields. Moreover, a gram-scale reaction and chemical transformation of the bridged ring by oxidation with m -CPBA were carried out to further extend the synthetic utility and the structural complexity.
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11
Total citations:
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Citations from 2025:
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(27.27%)
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Wen L. et al. GaCl3 catalyzed the cascade Michael/ketalization of o-hydroxychalcones with indoline-2-thiones: For the construction of indole-annulated 2-oxa-8-thiabicyclo[3.3.1]nonane derivatives // Tetrahedron Letters. 2022. Vol. 106. p. 154061.
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Wen L., Tang P., Ma H., Ren J., Yang Y., Jiang Y. GaCl3 catalyzed the cascade Michael/ketalization of o-hydroxychalcones with indoline-2-thiones: For the construction of indole-annulated 2-oxa-8-thiabicyclo[3.3.1]nonane derivatives // Tetrahedron Letters. 2022. Vol. 106. p. 154061.
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TY - JOUR
DO - 10.1016/j.tetlet.2022.154061
UR - https://doi.org/10.1016/j.tetlet.2022.154061
TI - GaCl3 catalyzed the cascade Michael/ketalization of o-hydroxychalcones with indoline-2-thiones: For the construction of indole-annulated 2-oxa-8-thiabicyclo[3.3.1]nonane derivatives
T2 - Tetrahedron Letters
AU - Wen, Long
AU - Tang, Pan
AU - Ma, Haojie
AU - Ren, Jin-Yao
AU - Yang, Yi
AU - Jiang, Yan
PY - 2022
DA - 2022/09/01
PB - Elsevier
SP - 154061
VL - 106
SN - 0040-4039
SN - 1873-3581
ER -
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@article{2022_Wen,
author = {Long Wen and Pan Tang and Haojie Ma and Jin-Yao Ren and Yi Yang and Yan Jiang},
title = {GaCl3 catalyzed the cascade Michael/ketalization of o-hydroxychalcones with indoline-2-thiones: For the construction of indole-annulated 2-oxa-8-thiabicyclo[3.3.1]nonane derivatives},
journal = {Tetrahedron Letters},
year = {2022},
volume = {106},
publisher = {Elsevier},
month = {sep},
url = {https://doi.org/10.1016/j.tetlet.2022.154061},
pages = {154061},
doi = {10.1016/j.tetlet.2022.154061}
}