volume 6 issue 10 pages 1681-1685

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
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 typeJournal Article
Publication date2019-04-02
scimago Q1
wos Q1
SJR1.068
CiteScore8.2
Impact factor4.7
ISSN20524110, 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.
Found 
Found 

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GOST Copy
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.
GOST all authors (up to 50) Copy
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.
RIS |
Cite this
RIS Copy
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 -
BibTex |
Cite this
BibTex (up to 50 authors) Copy
@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}
}
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.