Advanced Synthesis and Catalysis, volume 362, issue 23, pages 5467-5474
Optimization of Catalyst Structure for Asymmetric Propargylation of Aldehydes with Allenyltrichlorosilane
Vaganov Vladimir Yu
1
,
Fukazawa Yasuaki
2
,
Kondratyev Nikolay S
2
,
Shipilovskikh Sergei A
1, 2
,
Wheeler Steven E
3
,
Zhang Yuanjian
3
,
Malkov A. V.
2
,
Malkov Andrei V
2
3
Department of Chemistry University of Georgia Athens GA USA
|
Publication type: Journal Article
Publication date: 2020-10-16
Journal:
Advanced Synthesis and Catalysis
Quartile SCImago
Q1
Quartile WOS
Q1
Impact factor: 5.4
ISSN: 16154150, 16154169
General Chemistry
Abstract
The design of catalysts for asymmetric propargylations remains a challenging task, with only a handful of methods providing access to enantioenriched homopropargylic alcohols. In this work, guided by previously reported computational predictions, a set of atropisomeric bipyridine N,N’‐dioxides was tested as Lewis base catalysts for the asymmetric propargylation of aldehydes with trichloroallenylsilane. The catalysts are easily prepared in four simple steps starting from readily available methyl ketones. Aryl‐substituted derivatives proved to be highly active and showed a high level of enantiocontrol even at 1 mol% loading. The reaction scope includes a wide range of aromatic, heteroaromatic, and unsaturated aldehydes. New computations confirm that the key stereodetermining transition state structures for the synthesized catalysts are similar to those previously reported for the model structure.
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1 publication, 10%
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Citations by publishers
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1
2
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4 publications, 40%
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1 publication, 10%
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1 publication, 10%
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1 publication, 10%
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1 publication, 10%
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Elsevier
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Elsevier
1 publication, 10%
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Springer Nature
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Springer Nature
1 publication, 10%
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1
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3
4
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- We do not take into account publications that without a DOI.
- Statistics recalculated only for publications connected to researchers, organizations and labs registered on the platform.
- Statistics recalculated weekly.
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Vaganov V. Yu. et al. Optimization of Catalyst Structure for Asymmetric Propargylation of Aldehydes with Allenyltrichlorosilane // Advanced Synthesis and Catalysis. 2020. Vol. 362. No. 23. pp. 5467-5474.
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Vaganov V. Yu., Fukazawa Y., Kondratyev N. S., Shipilovskikh S. A., Zhang Y., Wheeler S. E., Rubtsov A. E., Malkov A. V., Malkov A. V. Optimization of Catalyst Structure for Asymmetric Propargylation of Aldehydes with Allenyltrichlorosilane // Advanced Synthesis and Catalysis. 2020. Vol. 362. No. 23. pp. 5467-5474.
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TY - JOUR
DO - 10.1002/adsc.202000936
UR - https://doi.org/10.1002%2Fadsc.202000936
TI - Optimization of Catalyst Structure for Asymmetric Propargylation of Aldehydes with Allenyltrichlorosilane
T2 - Advanced Synthesis and Catalysis
AU - Vaganov, Vladimir Yu
AU - Fukazawa, Yasuaki
AU - Kondratyev, Nikolay S
AU - Rubtsov, Aleksandr E
AU - Zhang, Yuanjian
AU - Malkov, A. V.
AU - Shipilovskikh, Sergei A
AU - Wheeler, Steven E
AU - Malkov, Andrei V
PY - 2020
DA - 2020/10/16 00:00:00
PB - Wiley
SP - 5467-5474
IS - 23
VL - 362
SN - 1615-4150
SN - 1615-4169
ER -
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@article{2020_Vaganov,
author = {Vladimir Yu Vaganov and Yasuaki Fukazawa and Nikolay S Kondratyev and Aleksandr E Rubtsov and Yuanjian Zhang and A. V. Malkov and Sergei A Shipilovskikh and Steven E Wheeler and Andrei V Malkov},
title = {Optimization of Catalyst Structure for Asymmetric Propargylation of Aldehydes with Allenyltrichlorosilane},
journal = {Advanced Synthesis and Catalysis},
year = {2020},
volume = {362},
publisher = {Wiley},
month = {oct},
url = {https://doi.org/10.1002%2Fadsc.202000936},
number = {23},
pages = {5467--5474},
doi = {10.1002/adsc.202000936}
}
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MLA
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Vaganov, Vladimir Yu., et al. “Optimization of Catalyst Structure for Asymmetric Propargylation of Aldehydes with Allenyltrichlorosilane.” Advanced Synthesis and Catalysis, vol. 362, no. 23, Oct. 2020, pp. 5467-5474. https://doi.org/10.1002%2Fadsc.202000936.
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