Journal of the American Chemical Society, volume 133, issue 27, pages 10582-10586
Diastereo- and Enantioselective Ruthenium-Catalyzed Hydrohydroxyalkylation of 2-Silyl-butadienes: Carbonylsyn-Crotylation from the Alcohol Oxidation Level
Publication type: Journal Article
Publication date: 2011-06-16
Quartile SCImago
Q1
Quartile WOS
Q1
Impact factor: 15
ISSN: 00027863, 15205126
General Chemistry
Catalysis
Biochemistry
Colloid and Surface Chemistry
Abstract
Exposure of alcohols 2a-2j to 2-silyl-butadienes in the presence of ruthenium complexes modified by (R)-SEGPHOS or (R)-DM-SEGPHOS results in redox-triggered generation of allylruthenium-aldehyde pairs, which combine to form products of carbonyl crotylation 4a-4j in the absence of stoichiometric byproducts and with high levels of syn-diastereo- and enantioselectivity. In the presence of isopropanol under otherwise identical conditions, aldehydes 3a-3j are converted to an equivalent set of adducts 4a-4j. Whereas reactions conducted using conventional heating require 48 h, microwave irradiation enables full conversion in only 4 h. Finally, as illustrated in the conversion of adduct 4a to compounds 6a and 6b, diastereoselective hydroboration-Suzuki cross-coupling with aryl and vinyl halides followed by Fleming-Tamao oxidation enables generation of anti,syn-stereotriads found in numerous polyketide natural products.
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Citations by publishers
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10
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Wiley
52 publications, 38.52%
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American Chemical Society (ACS)
51 publications, 37.78%
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Elsevier
5 publications, 3.7%
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3 publications, 2.22%
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2 publications, 1.48%
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1 publication, 0.74%
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Taylor & Francis
1 publication, 0.74%
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Walter de Gruyter
1 publication, 0.74%
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Thieme
1 publication, 0.74%
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Autonomous Non-profit Organization Editorial Board of the journal Uspekhi Khimii
1 publication, 0.74%
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- We do not take into account publications 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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Zbieg J. R., Moran J., Krische M. J. Diastereo- and Enantioselective Ruthenium-Catalyzed Hydrohydroxyalkylation of 2-Silyl-butadienes: Carbonylsyn-Crotylation from the Alcohol Oxidation Level // Journal of the American Chemical Society. 2011. Vol. 133. No. 27. pp. 10582-10586.
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Zbieg J. R., Moran J., Krische M. J. Diastereo- and Enantioselective Ruthenium-Catalyzed Hydrohydroxyalkylation of 2-Silyl-butadienes: Carbonylsyn-Crotylation from the Alcohol Oxidation Level // Journal of the American Chemical Society. 2011. Vol. 133. No. 27. pp. 10582-10586.
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TY - JOUR
DO - 10.1021/ja2046028
UR - https://doi.org/10.1021/ja2046028
TI - Diastereo- and Enantioselective Ruthenium-Catalyzed Hydrohydroxyalkylation of 2-Silyl-butadienes: Carbonylsyn-Crotylation from the Alcohol Oxidation Level
T2 - Journal of the American Chemical Society
AU - Zbieg, Jason R
AU - Moran, Joseph
AU - Krische, Michael J
PY - 2011
DA - 2011/06/16 00:00:00
PB - American Chemical Society (ACS)
SP - 10582-10586
IS - 27
VL - 133
SN - 0002-7863
SN - 1520-5126
ER -
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@article{2011_Zbieg,
author = {Jason R Zbieg and Joseph Moran and Michael J Krische},
title = {Diastereo- and Enantioselective Ruthenium-Catalyzed Hydrohydroxyalkylation of 2-Silyl-butadienes: Carbonylsyn-Crotylation from the Alcohol Oxidation Level},
journal = {Journal of the American Chemical Society},
year = {2011},
volume = {133},
publisher = {American Chemical Society (ACS)},
month = {jun},
url = {https://doi.org/10.1021/ja2046028},
number = {27},
pages = {10582--10586},
doi = {10.1021/ja2046028}
}
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MLA
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Zbieg, Jason R., et al. “Diastereo- and Enantioselective Ruthenium-Catalyzed Hydrohydroxyalkylation of 2-Silyl-butadienes: Carbonylsyn-Crotylation from the Alcohol Oxidation Level.” Journal of the American Chemical Society, vol. 133, no. 27, Jun. 2011, pp. 10582-10586. https://doi.org/10.1021/ja2046028.