Chiral DMAP‐ N ‐oxides as Acyl Transfer Catalysts: Design, Synthesis, and Application in Asymmetric Steglich Rearrangement
Тип публикации: Journal Article
Дата публикации: 2019-02-25
scimago Q1
wos Q1
БС1
SJR: 5.550
CiteScore: 27.6
Impact factor: 16.9
ISSN: 14337851, 15213773
PubMed ID:
30653794
General Chemistry
Catalysis
Краткое описание
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.
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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.
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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.
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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 -
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@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}
}
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MLA
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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.