Chiral DMAP‐ N ‐oxides as Acyl Transfer Catalysts: Design, Synthesis, and Application in Asymmetric Steglich Rearrangement
Publication type: Journal Article
Publication date: 2019-02-25
scimago Q1
wos Q1
SJR: 5.550
CiteScore: 27.6
Impact factor: 16.9
ISSN: 14337851, 15213773
PubMed ID:
30653794
General Chemistry
Catalysis
Abstract
A DMAP-N-oxide, featuring an α-amino acid as the chiral source, was developed, synthesized and applied in asymmetric Steglich rearrangement. A series of O-acylated azlactones afforded C-acylated azlactones possessing a quaternary stereocenter in high yields (up to 97 % yield) and excellent enantioselectivities (up to 97 % ee). Compared to the widespread use of pyridine nitrogen, which serves as the nucleophilic site in the asymmetric acyl transfer reaction, we discovered that chiral DMAP-N-oxides, in which the oxygen now acts as the nucleophilic site, are efficient acyl transfer catalysts. Our finding might open a new door for the development of chiral DMAP-N-oxides for asymmetric acyl transfer reactions.
Found
Nothing found, try to update filter.
Found
Nothing found, try to update filter.
Top-30
Journals
|
1
2
3
4
5
6
7
8
|
|
|
Organic Chemistry Frontiers
8 publications, 15.38%
|
|
|
ACS Catalysis
7 publications, 13.46%
|
|
|
Organic Letters
6 publications, 11.54%
|
|
|
Journal of the American Chemical Society
4 publications, 7.69%
|
|
|
Chemical Science
4 publications, 7.69%
|
|
|
ChemCatChem
3 publications, 5.77%
|
|
|
Journal of Organic Chemistry
3 publications, 5.77%
|
|
|
Frontiers in Chemistry
1 publication, 1.92%
|
|
|
Science China Chemistry
1 publication, 1.92%
|
|
|
Chemical Physics Letters
1 publication, 1.92%
|
|
|
ChemistrySelect
1 publication, 1.92%
|
|
|
European Journal of Organic Chemistry
1 publication, 1.92%
|
|
|
Angewandte Chemie - International Edition
1 publication, 1.92%
|
|
|
Angewandte Chemie
1 publication, 1.92%
|
|
|
ChemSusChem
1 publication, 1.92%
|
|
|
Organic and Biomolecular Chemistry
1 publication, 1.92%
|
|
|
Communications Chemistry
1 publication, 1.92%
|
|
|
Chemistry - A European Journal
1 publication, 1.92%
|
|
|
Nature Chemistry
1 publication, 1.92%
|
|
|
Advanced Science
1 publication, 1.92%
|
|
|
Tetrahedron
1 publication, 1.92%
|
|
|
Scientia Sinica Chimica
1 publication, 1.92%
|
|
|
Chemical Society Reviews
1 publication, 1.92%
|
|
|
Macromolecules
1 publication, 1.92%
|
|
|
1
2
3
4
5
6
7
8
|
Publishers
|
5
10
15
20
25
|
|
|
American Chemical Society (ACS)
21 publications, 40.38%
|
|
|
Royal Society of Chemistry (RSC)
14 publications, 26.92%
|
|
|
Wiley
10 publications, 19.23%
|
|
|
Springer Nature
3 publications, 5.77%
|
|
|
Elsevier
2 publications, 3.85%
|
|
|
Frontiers Media S.A.
1 publication, 1.92%
|
|
|
Science in China Press
1 publication, 1.92%
|
|
|
5
10
15
20
25
|
- We do not take into account publications without a DOI.
- Statistics recalculated weekly.
Are you a researcher?
Create a profile to get free access to personal recommendations for colleagues and new articles.
Metrics
52
Total citations:
52
Citations from 2024:
15
(28.84%)
Cite this
GOST |
RIS |
BibTex |
MLA
Cite this
GOST
Copy
Xie M. et al. Chiral DMAP‐ N ‐oxides as Acyl Transfer Catalysts: Design, Synthesis, and Application in Asymmetric Steglich Rearrangement // Angewandte Chemie - International Edition. 2019. Vol. 58. No. 9. pp. 2839-2843.
GOST all authors (up to 50)
Copy
Xie M., Zhang Y., Shan M., Wu X., Gui-Rong Q., Guo H. Chiral DMAP‐ N ‐oxides as Acyl Transfer Catalysts: Design, Synthesis, and Application in Asymmetric Steglich Rearrangement // Angewandte Chemie - International Edition. 2019. Vol. 58. No. 9. pp. 2839-2843.
Cite this
RIS
Copy
TY - JOUR
DO - 10.1002/anie.201812864
UR - https://doi.org/10.1002/anie.201812864
TI - Chiral DMAP‐ N ‐oxides as Acyl Transfer Catalysts: Design, Synthesis, and Application in Asymmetric Steglich Rearrangement
T2 - Angewandte Chemie - International Edition
AU - Xie, Mingsheng
AU - Zhang, Ye-Fei
AU - Shan, Meng
AU - Wu, Xiao-Xia
AU - Gui-Rong, Qu
AU - Guo, Haiming
PY - 2019
DA - 2019/02/25
PB - Wiley
SP - 2839-2843
IS - 9
VL - 58
PMID - 30653794
SN - 1433-7851
SN - 1521-3773
ER -
Cite this
BibTex (up to 50 authors)
Copy
@article{2019_Xie,
author = {Mingsheng Xie and Ye-Fei Zhang and Meng Shan and Xiao-Xia Wu and Qu Gui-Rong and Haiming Guo},
title = {Chiral DMAP‐ N ‐oxides as Acyl Transfer Catalysts: Design, Synthesis, and Application in Asymmetric Steglich Rearrangement},
journal = {Angewandte Chemie - International Edition},
year = {2019},
volume = {58},
publisher = {Wiley},
month = {feb},
url = {https://doi.org/10.1002/anie.201812864},
number = {9},
pages = {2839--2843},
doi = {10.1002/anie.201812864}
}
Cite this
MLA
Copy
Xie, Mingsheng, et al. “Chiral DMAP‐ N ‐oxides as Acyl Transfer Catalysts: Design, Synthesis, and Application in Asymmetric Steglich Rearrangement.” Angewandte Chemie - International Edition, vol. 58, no. 9, Feb. 2019, pp. 2839-2843. https://doi.org/10.1002/anie.201812864.