Journal of Organic Chemistry, volume 85, issue 17, pages 11060-11071
Asymmetric Synthesis of Merck’s Potent hNK1 Antagonist and Its Stereoisomers via Tandem Acylation/[3,3]-Rearrangement of 1,2-Oxazine N-Oxides
Publication type: Journal Article
Publication date: 2020-08-11
Journal:
Journal of Organic Chemistry
Quartile SCImago
Q1
Quartile WOS
Q1
Impact factor: 3.6
ISSN: 00223263, 15206904
Organic Chemistry
Abstract
An asymmetric total synthesis of Merck's hNK1 antagonist and three of its stereoisomers was accomplished in 10 steps. The synthesis involves a stereoselective assembly of 1,2-oxazine N-oxide by the [4 + 2]-cycloaddition, site-selective C-H oxygenation using a novel tandem acylation/[3,3]-rearrangement process and the reductive 1,2-oxazine ring contraction into a pyrrolidine ring as key stages. Using this strategy, the fused pyrrolidine subunit was constructed with exceptionally high regio- and stereoselectivities. The approach described here can be used to access enantiopure 3,4-disubstituted prolinols, which are frequently found in pharmaceutically relevant molecules and organocatalysts.
Citations by journals
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European Journal of Organic Chemistry
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European Journal of Organic Chemistry
2 publications, 25%
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Journal of Organic Chemistry
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Journal of Organic Chemistry
1 publication, 12.5%
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Molecules
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Molecules
1 publication, 12.5%
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Chemical Communications
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Chemical Communications
1 publication, 12.5%
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Organic and Biomolecular Chemistry
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Organic and Biomolecular Chemistry
1 publication, 12.5%
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Synfacts
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Synfacts
1 publication, 12.5%
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Catalysts
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Catalysts
1 publication, 12.5%
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1
2
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Citations by publishers
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1
2
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Wiley
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Wiley
2 publications, 25%
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Multidisciplinary Digital Publishing Institute (MDPI)
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Multidisciplinary Digital Publishing Institute (MDPI)
2 publications, 25%
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Royal Society of Chemistry (RSC)
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Royal Society of Chemistry (RSC)
2 publications, 25%
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American Chemical Society (ACS)
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American Chemical Society (ACS)
1 publication, 12.5%
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Thieme
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Thieme
1 publication, 12.5%
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1
2
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- We do not take into account publications that without a DOI.
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- Statistics recalculated weekly.
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Dorokhov V. S. et al. Asymmetric Synthesis of Merck’s Potent hNK1 Antagonist and Its Stereoisomers via Tandem Acylation/[3,3]-Rearrangement of 1,2-Oxazine N-Oxides // Journal of Organic Chemistry. 2020. Vol. 85. No. 17. pp. 11060-11071.
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Dorokhov V. S., Nelyubina Y. V., Ioffe S. L., Sukhorukov A. Yu. Asymmetric Synthesis of Merck’s Potent hNK1 Antagonist and Its Stereoisomers via Tandem Acylation/[3,3]-Rearrangement of 1,2-Oxazine N-Oxides // Journal of Organic Chemistry. 2020. Vol. 85. No. 17. pp. 11060-11071.
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TY - JOUR
DO - 10.1021/acs.joc.0c01322
UR - https://doi.org/10.1021%2Facs.joc.0c01322
TI - Asymmetric Synthesis of Merck’s Potent hNK1 Antagonist and Its Stereoisomers via Tandem Acylation/[3,3]-Rearrangement of 1,2-Oxazine N-Oxides
T2 - Journal of Organic Chemistry
AU - Sukhorukov, Alexey Yu
AU - Dorokhov, Valentin S
AU - Nelyubina, Yulia V.
AU - Ioffe, Sema L.
PY - 2020
DA - 2020/08/11 00:00:00
PB - American Chemical Society (ACS)
SP - 11060-11071
IS - 17
VL - 85
SN - 0022-3263
SN - 1520-6904
ER -
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@article{2020_Dorokhov,
author = {Alexey Yu Sukhorukov and Valentin S Dorokhov and Yulia V. Nelyubina and Sema L. Ioffe},
title = {Asymmetric Synthesis of Merck’s Potent hNK1 Antagonist and Its Stereoisomers via Tandem Acylation/[3,3]-Rearrangement of 1,2-Oxazine N-Oxides},
journal = {Journal of Organic Chemistry},
year = {2020},
volume = {85},
publisher = {American Chemical Society (ACS)},
month = {aug},
url = {https://doi.org/10.1021%2Facs.joc.0c01322},
number = {17},
pages = {11060--11071},
doi = {10.1021/acs.joc.0c01322}
}
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MLA
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Dorokhov, Valentin S., et al. “Asymmetric Synthesis of Merck’s Potent hNK1 Antagonist and Its Stereoisomers via Tandem Acylation/[3,3]-Rearrangement of 1,2-Oxazine N-Oxides.” Journal of Organic Chemistry, vol. 85, no. 17, Aug. 2020, pp. 11060-11071. https://doi.org/10.1021%2Facs.joc.0c01322.
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