Insights into the diastereoselective control in the sulfa-Michael addition of thiols to nitroalkenes: stereoelectronic effect in the cyclic chelated transition state
Publication type: Journal Article
Publication date: 2016-01-01
scimago Q3
wos Q2
SJR: 0.426
CiteScore: 4.1
Impact factor: 2.2
ISSN: 00404020, 14645416
Organic Chemistry
Drug Discovery
Biochemistry
Abstract
The diastereoselective control in the sulfa-Michael addition of nitroalkenes and lithium thiolates followed by protonation was investigated. Lithium thiolates first added to nitroalkenes to afford cyclic lithium-chelated nitronates. The subsequent kinetic protonation of nitronates was proved to be the stereochemical determinant through the chelate-controlled six-membered half-chair transition state bearing two approximately 1,2-diaxial substituents due to stereoelectronic effect control. The stereoelectronic effect in the cyclic chelated transition state was probed and verified by tuning the steric bulkiness of the corresponding substituents. The reaction involving 1-nitrocyclohexene provided perfect support for the proposed diastereoselective control model. The current investigation provided not only comprehensive insights into the diastereoselective control in the sulfa-Michael addition of nitroalkenes and thiolates, but also an important role of the stereoelectronic effect in certain organic reactions involving cyclic chelate transition states.
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Total citations:
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Citations from 2025:
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(11.11%)
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Wang J. et al. Insights into the diastereoselective control in the sulfa-Michael addition of thiols to nitroalkenes: stereoelectronic effect in the cyclic chelated transition state // Tetrahedron. 2016. Vol. 72. No. 3. pp. 370-378.
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Wang J., Li P., Yang Z., Chen N., Xu J. Insights into the diastereoselective control in the sulfa-Michael addition of thiols to nitroalkenes: stereoelectronic effect in the cyclic chelated transition state // Tetrahedron. 2016. Vol. 72. No. 3. pp. 370-378.
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TY - JOUR
DO - 10.1016/j.tet.2015.11.030
UR - https://doi.org/10.1016/j.tet.2015.11.030
TI - Insights into the diastereoselective control in the sulfa-Michael addition of thiols to nitroalkenes: stereoelectronic effect in the cyclic chelated transition state
T2 - Tetrahedron
AU - Wang, Jiandong
AU - Li, Pingfan
AU - Yang, Zhanhui
AU - Chen, Ning
AU - Xu, Jiaxi
PY - 2016
DA - 2016/01/01
PB - Elsevier
SP - 370-378
IS - 3
VL - 72
SN - 0040-4020
SN - 1464-5416
ER -
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BibTex (up to 50 authors)
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@article{2016_Wang,
author = {Jiandong Wang and Pingfan Li and Zhanhui Yang and Ning Chen and Jiaxi Xu},
title = {Insights into the diastereoselective control in the sulfa-Michael addition of thiols to nitroalkenes: stereoelectronic effect in the cyclic chelated transition state},
journal = {Tetrahedron},
year = {2016},
volume = {72},
publisher = {Elsevier},
month = {jan},
url = {https://doi.org/10.1016/j.tet.2015.11.030},
number = {3},
pages = {370--378},
doi = {10.1016/j.tet.2015.11.030}
}
Cite this
MLA
Copy
Wang, Jiandong, et al. “Insights into the diastereoselective control in the sulfa-Michael addition of thiols to nitroalkenes: stereoelectronic effect in the cyclic chelated transition state.” Tetrahedron, vol. 72, no. 3, Jan. 2016, pp. 370-378. https://doi.org/10.1016/j.tet.2015.11.030.