Synergistic Dual Directing Groups-Enabled Diastereoselective C-H Cyclopropylation via Rh(III)-Catalyzed Couplings with Cyclopropenyl Alcohols.
Publication type: Journal Article
Publication date: 2020-02-04
scimago Q1
wos Q1
SJR: 1.235
CiteScore: 8.7
Impact factor: 5.0
ISSN: 15237060, 15237052
PubMed ID:
32017582
Organic Chemistry
Biochemistry
Physical and Theoretical Chemistry
Abstract
By using a synergistic dual directing group-assisted C-H activation strategy and simply modifying the reaction conditions, we realized a robust and general Cp*Rh(III)-catalyzed C-H cyclopropylation of N-acetoxybenzamides with cyclopropenyl alcohols, providing regio-, chemo-, and diastereoselective access to ortho trans- and cis-1,1-dimethylcyclopropane-functionalized benzamides in a redox-neutral and controllable manner. Experimental and density functional theory studies clarify the roles of the NH-OAc and OH groups and deduce two distinct Rh(III)-Rh(V)-Rh(III) pathways for presenting such selectivity.
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Wu M. et al. Synergistic Dual Directing Groups-Enabled Diastereoselective C-H Cyclopropylation via Rh(III)-Catalyzed Couplings with Cyclopropenyl Alcohols. // Organic Letters. 2020. Vol. 22. No. 4. pp. 1295-1300.
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Wu M., Lin S., Zhu G., Sun M., Zhou Z., Gao H., Yi W. Synergistic Dual Directing Groups-Enabled Diastereoselective C-H Cyclopropylation via Rh(III)-Catalyzed Couplings with Cyclopropenyl Alcohols. // Organic Letters. 2020. Vol. 22. No. 4. pp. 1295-1300.
Cite this
RIS
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TY - JOUR
DO - 10.1021/acs.orglett.9b04608
UR - https://doi.org/10.1021/acs.orglett.9b04608
TI - Synergistic Dual Directing Groups-Enabled Diastereoselective C-H Cyclopropylation via Rh(III)-Catalyzed Couplings with Cyclopropenyl Alcohols.
T2 - Organic Letters
AU - Wu, Min
AU - Lin, Shuang
AU - Zhu, Guoxun
AU - Sun, Ming
AU - Zhou, Zhi
AU - Gao, Hui
AU - Yi, Wei
PY - 2020
DA - 2020/02/04
PB - American Chemical Society (ACS)
SP - 1295-1300
IS - 4
VL - 22
PMID - 32017582
SN - 1523-7060
SN - 1523-7052
ER -
Cite this
BibTex (up to 50 authors)
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@article{2020_Wu,
author = {Min Wu and Shuang Lin and Guoxun Zhu and Ming Sun and Zhi Zhou and Hui Gao and Wei Yi},
title = {Synergistic Dual Directing Groups-Enabled Diastereoselective C-H Cyclopropylation via Rh(III)-Catalyzed Couplings with Cyclopropenyl Alcohols.},
journal = {Organic Letters},
year = {2020},
volume = {22},
publisher = {American Chemical Society (ACS)},
month = {feb},
url = {https://doi.org/10.1021/acs.orglett.9b04608},
number = {4},
pages = {1295--1300},
doi = {10.1021/acs.orglett.9b04608}
}
Cite this
MLA
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Wu, Min, et al. “Synergistic Dual Directing Groups-Enabled Diastereoselective C-H Cyclopropylation via Rh(III)-Catalyzed Couplings with Cyclopropenyl Alcohols..” Organic Letters, vol. 22, no. 4, Feb. 2020, pp. 1295-1300. https://doi.org/10.1021/acs.orglett.9b04608.