Angewandte Chemie - International Edition, volume 50, issue 18, pages 4173-4175
Iridium-Catalyzed anti-Diastereo- and Enantioselective Carbonyl (α-Trifluoromethyl)allylation from the Alcohol or Aldehyde Oxidation Level
Publication type: Journal Article
Publication date: 2011-04-06
Quartile SCImago
Q1
Quartile WOS
Q1
Impact factor: 16.6
ISSN: 14337851, 15213773
General Chemistry
Catalysis
Abstract
Using the ortho-cyclometalated π-allyl iridium precatalyst (R)-I derived from [Ir(cod)Cl]2, 4-cyano-3-nitrobenzoic acid, (R)-SEGPHOS, and allyl acetate, enantioselective transfer hydrogenation of α-(trimethylsilyl)allyl acetate in the presence of aldehydes 2a−i mediated by 2-propanol delivers products of (trimethylsilyl)allylation 4a−i in good isolated yields and with exceptional levels of anti-diastereoselectivity and enantioselectivity (90−99% ee). In the absence of 2-propanol, but under otherwise identical reaction conditions, carbonyl (trimethylsilyl)allylation is achieved directly from the alcohol oxidation level to furnish an equivalent set of adducts 4a−i with roughly equivalent isolated yields and stereoselectivities. To evaluate the synthetic utility of the reaction products 4a−i, adduct 4g was converted to the 1,4-ene-diol 5g via dioxirane-mediated oxidative desilylation with allylic transposition, the allylic alcohol 6g via protodesilylation with allylic transposition, and the γ-lactam 7g via c...
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Citations by publishers
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American Chemical Society (ACS)
16 publications, 34.04%
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1 publication, 2.13%
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Springer Nature
1 publication, 2.13%
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Thieme
1 publication, 2.13%
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1 publication, 2.13%
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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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Gao X., Zhang Y. J., Krische M. J. Iridium-Catalyzed anti-Diastereo- and Enantioselective Carbonyl (α-Trifluoromethyl)allylation from the Alcohol or Aldehyde Oxidation Level // Angewandte Chemie - International Edition. 2011. Vol. 50. No. 18. pp. 4173-4175.
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Gao X., Zhang Y. J., Krische M. J. Iridium-Catalyzed anti-Diastereo- and Enantioselective Carbonyl (α-Trifluoromethyl)allylation from the Alcohol or Aldehyde Oxidation Level // Angewandte Chemie - International Edition. 2011. Vol. 50. No. 18. pp. 4173-4175.
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TY - JOUR
DO - 10.1002/anie.201008296
UR - https://doi.org/10.1002/anie.201008296
TI - Iridium-Catalyzed anti-Diastereo- and Enantioselective Carbonyl (α-Trifluoromethyl)allylation from the Alcohol or Aldehyde Oxidation Level
T2 - Angewandte Chemie - International Edition
AU - Gao, Xin
AU - Zhang, Yong Jian
AU - Krische, Michael J
PY - 2011
DA - 2011/04/06 00:00:00
PB - Wiley
SP - 4173-4175
IS - 18
VL - 50
SN - 1433-7851
SN - 1521-3773
ER -
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@article{2011_Gao,
author = {Xin Gao and Yong Jian Zhang and Michael J Krische},
title = {Iridium-Catalyzed anti-Diastereo- and Enantioselective Carbonyl (α-Trifluoromethyl)allylation from the Alcohol or Aldehyde Oxidation Level},
journal = {Angewandte Chemie - International Edition},
year = {2011},
volume = {50},
publisher = {Wiley},
month = {apr},
url = {https://doi.org/10.1002/anie.201008296},
number = {18},
pages = {4173--4175},
doi = {10.1002/anie.201008296}
}
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MLA
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Gao, Xin, et al. “Iridium-Catalyzed anti-Diastereo- and Enantioselective Carbonyl (α-Trifluoromethyl)allylation from the Alcohol or Aldehyde Oxidation Level.” Angewandte Chemie - International Edition, vol. 50, no. 18, Apr. 2011, pp. 4173-4175. https://doi.org/10.1002/anie.201008296.