Carboxylate phosphabetaine as a bifunctional organocatalyst for the intramolecular ring opening of oxetane
Dongyang Xu
1, 2, 3, 4, 5, 6
,
Hongbo Wei
1
,
Yanxia Zhen
1, 2, 3, 4, 5, 6
,
Yu-Qi Gao
1, 2, 3, 4, 5, 6
,
Ruoxin Li
1, 2, 3, 4, 5, 6
,
Xingzhou Li
7, 8, 9, 10, 11
,
Yu Peng He
12
,
Yupeng He
6, 13, 14, 15, 16
,
Zhong Zhang
1, 2, 3, 4, 5, 6
,
Weiqing Xie
1, 2, 3, 4, 5, 6, 17
1
2
Shaanxi Key Laboratory of Natural Products & Chemical Biology
3
College of Chemistry & Pharmacy
5
Yangling 712100
|
6
CHINA
|
7
Laboratory of Computer-Aided Drug Design & Discovery, Beijing Institute of Pharmacology and Toxicology, 27 Taiping Road, Beijing 100850, P.R. China
|
8
Laboratory of Computer-Aided Drug Design & Discovery
9
Beijing Institute of Pharmacology and Toxicology
|
10
Beijing 100850
|
11
P.R. China
|
12
College of Chemistry, Chemical Engineering and Environmental Engineering, Liaoning Shihua University, Dandong Lu West 1, Fushun 113001, China
|
13
College of Chemistry
14
Chemical Engineering and Environmental Engineering
15
Liaoning ShiHua University
16
Fushun 113001
|
17
Key Laboratory of Botanical Pesticide R&D in Shaanxi Province, Yangling, Shaanxi 712100, China
|
Publication type: Journal Article
Publication date: 2019-04-02
scimago Q1
wos Q1
SJR: 1.068
CiteScore: 8.2
Impact factor: 4.7
ISSN: 20524110, 20524129
Organic Chemistry
Abstract
Herein, we disclose that carboxylate phosphabetaine can act as a competent organocatalyst for promoting the intramolecular ring opening of oxetanes, delivering oxazolidin-2-ones in good to excellent yields. 1H NMR studies and DFT calculations revealed that the carboxylate moiety of the phosphabetaine not only acts as a proton shuttle, but also provides crucial hydrogen bonding for the activation of the oxetane ring.
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Total citations:
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Citations from 2025:
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GOST
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Xu D. et al. Carboxylate phosphabetaine as a bifunctional organocatalyst for the intramolecular ring opening of oxetane // Organic Chemistry Frontiers. 2019. Vol. 6. No. 10. pp. 1681-1685.
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Xu D., Wei H., Zhen Y., Gao Y., Li R., Li X., He Yu. P., He Y., Zhang Z., Xie W. Carboxylate phosphabetaine as a bifunctional organocatalyst for the intramolecular ring opening of oxetane // Organic Chemistry Frontiers. 2019. Vol. 6. No. 10. pp. 1681-1685.
Cite this
RIS
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TY - JOUR
DO - 10.1039/c9qo00304e
UR - https://xlink.rsc.org/?DOI=C9QO00304E
TI - Carboxylate phosphabetaine as a bifunctional organocatalyst for the intramolecular ring opening of oxetane
T2 - Organic Chemistry Frontiers
AU - Xu, Dongyang
AU - Wei, Hongbo
AU - Zhen, Yanxia
AU - Gao, Yu-Qi
AU - Li, Ruoxin
AU - Li, Xingzhou
AU - He, Yu Peng
AU - He, Yupeng
AU - Zhang, Zhong
AU - Xie, Weiqing
PY - 2019
DA - 2019/04/02
PB - Royal Society of Chemistry (RSC)
SP - 1681-1685
IS - 10
VL - 6
SN - 2052-4110
SN - 2052-4129
ER -
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@article{2019_Xu,
author = {Dongyang Xu and Hongbo Wei and Yanxia Zhen and Yu-Qi Gao and Ruoxin Li and Xingzhou Li and Yu Peng He and Yupeng He and Zhong Zhang and Weiqing Xie},
title = {Carboxylate phosphabetaine as a bifunctional organocatalyst for the intramolecular ring opening of oxetane},
journal = {Organic Chemistry Frontiers},
year = {2019},
volume = {6},
publisher = {Royal Society of Chemistry (RSC)},
month = {apr},
url = {https://xlink.rsc.org/?DOI=C9QO00304E},
number = {10},
pages = {1681--1685},
doi = {10.1039/c9qo00304e}
}
Cite this
MLA
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Xu, Dongyang, et al. “Carboxylate phosphabetaine as a bifunctional organocatalyst for the intramolecular ring opening of oxetane.” Organic Chemistry Frontiers, vol. 6, no. 10, Apr. 2019, pp. 1681-1685. https://xlink.rsc.org/?DOI=C9QO00304E.