Advanced Synthesis and Catalysis, volume 361, issue 23, pages 5322-5327
Synthesis of Isoxazolines from Nitroalkanes via a [4+1]‐Annulation Strategy
Pavel Yu Ushakov
1, 2
,
Elizaveta A Khatuntseva
1
,
Andrey A Tabolin
1
,
Sema L. Ioffe
1
,
Alexey Yu Sukhorukov
1, 4, 5
Publication type: Journal Article
Publication date: 2019-10-22
Journal:
Advanced Synthesis and Catalysis
Quartile SCImago
Q1
Quartile WOS
Q1
Impact factor: 4.4
ISSN: 16154150, 16154169
General Chemistry
Abstract
A novel access to isoxazolines was developed using the [4+1]‐annulation of α‐keto‐stabilized sulfur ylides with N,N‐bis(siloxy)enamines derived from aliphatic nitro compounds. The resulting 5‐keto‐substituted isoxazolines were shown to be convenient precursors of polysubstituted 3‐hydroxypyrrolidines via the one‐pot catalytic N−O hydrogenolysis/intramolecular reductive amination sequence. Application of this approach to the formal synthesis of Merck's potent NK1 receptor antagonist was demonstrated.
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GOST
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Ushakov P. Yu. et al. Synthesis of Isoxazolines from Nitroalkanes via a [4+1]‐Annulation Strategy // Advanced Synthesis and Catalysis. 2019. Vol. 361. No. 23. pp. 5322-5327.
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Ushakov P. Yu., Khatuntseva E. A., Nelyubina Y. V., Tabolin A. A., Ioffe S. L., Sukhorukov A. Yu. Synthesis of Isoxazolines from Nitroalkanes via a [4+1]‐Annulation Strategy // Advanced Synthesis and Catalysis. 2019. Vol. 361. No. 23. pp. 5322-5327.
Cite this
RIS
Copy
TY - JOUR
DO - 10.1002/adsc.201901000
UR - https://onlinelibrary.wiley.com/doi/10.1002/adsc.201901000
TI - Synthesis of Isoxazolines from Nitroalkanes via a [4+1]‐Annulation Strategy
T2 - Advanced Synthesis and Catalysis
AU - Ushakov, Pavel Yu
AU - Khatuntseva, Elizaveta A
AU - Nelyubina, Yulia V.
AU - Tabolin, Andrey A
AU - Ioffe, Sema L.
AU - Sukhorukov, Alexey Yu
PY - 2019
DA - 2019/10/22
PB - Wiley
SP - 5322-5327
IS - 23
VL - 361
SN - 1615-4150
SN - 1615-4169
ER -
Cite this
BibTex
Copy
@article{2019_Ushakov,
author = {Pavel Yu Ushakov and Elizaveta A Khatuntseva and Yulia V. Nelyubina and Andrey A Tabolin and Sema L. Ioffe and Alexey Yu Sukhorukov},
title = {Synthesis of Isoxazolines from Nitroalkanes via a [4+1]‐Annulation Strategy},
journal = {Advanced Synthesis and Catalysis},
year = {2019},
volume = {361},
publisher = {Wiley},
month = {oct},
url = {https://onlinelibrary.wiley.com/doi/10.1002/adsc.201901000},
number = {23},
pages = {5322--5327},
doi = {10.1002/adsc.201901000}
}
Cite this
MLA
Copy
Ushakov, Pavel Yu., et al. “Synthesis of Isoxazolines from Nitroalkanes via a [4+1]‐Annulation Strategy.” Advanced Synthesis and Catalysis, vol. 361, no. 23, Oct. 2019, pp. 5322-5327. https://onlinelibrary.wiley.com/doi/10.1002/adsc.201901000.
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