Journal of the American Chemical Society, volume 132, issue 26, pages 9153-9156
Iridium-Catalyzed anti-Diastereo- and Enantioselective Carbonyl (Trimethylsilyl)allylation from the Alcohol or Aldehyde Oxidation Level
Publication type: Journal Article
Publication date: 2010-06-11
Quartile SCImago
Q1
Quartile WOS
Q1
Impact factor: 15
ISSN: 00027863, 15205126
General Chemistry
Catalysis
Biochemistry
Colloid and Surface Chemistry
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 chlorosulfonyl isocyanate-mediated cycloaddition.
Top-30
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1 publication, 1.41%
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1 publication, 1.41%
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1 publication, 1.41%
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1 publication, 1.41%
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1 publication, 1.41%
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1 publication, 1.41%
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1 publication, 1.41%
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1 publication, 1.41%
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1 publication, 1.41%
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1 publication, 1.41%
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1 publication, 1.41%
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1 publication, 1.41%
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1 publication, 1.41%
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1 publication, 1.41%
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2
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Citations by publishers
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5
10
15
20
25
30
35
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Wiley
33 publications, 46.48%
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American Chemical Society (ACS)
18 publications, 25.35%
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Royal Society of Chemistry (RSC)
7 publications, 9.86%
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Elsevier
5 publications, 7.04%
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Springer Nature
3 publications, 4.23%
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Shanghai Institute of Organic Chemistry
1 publication, 1.41%
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Thieme
1 publication, 1.41%
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Autonomous Non-profit Organization Editorial Board of the journal Uspekhi Khimii
1 publication, 1.41%
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5
10
15
20
25
30
35
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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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Han S. B., Gao X., Krische M. J. Iridium-Catalyzed anti-Diastereo- and Enantioselective Carbonyl (Trimethylsilyl)allylation from the Alcohol or Aldehyde Oxidation Level // Journal of the American Chemical Society. 2010. Vol. 132. No. 26. pp. 9153-9156.
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Han S. B., Gao X., Krische M. J. Iridium-Catalyzed anti-Diastereo- and Enantioselective Carbonyl (Trimethylsilyl)allylation from the Alcohol or Aldehyde Oxidation Level // Journal of the American Chemical Society. 2010. Vol. 132. No. 26. pp. 9153-9156.
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TY - JOUR
DO - 10.1021/ja103299f
UR - https://doi.org/10.1021/ja103299f
TI - Iridium-Catalyzed anti-Diastereo- and Enantioselective Carbonyl (Trimethylsilyl)allylation from the Alcohol or Aldehyde Oxidation Level
T2 - Journal of the American Chemical Society
AU - Han, Soo Bong
AU - Gao, Xin
AU - Krische, Michael J
PY - 2010
DA - 2010/06/11 00:00:00
PB - American Chemical Society (ACS)
SP - 9153-9156
IS - 26
VL - 132
SN - 0002-7863
SN - 1520-5126
ER -
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@article{2010_Han,
author = {Soo Bong Han and Xin Gao and Michael J Krische},
title = {Iridium-Catalyzed anti-Diastereo- and Enantioselective Carbonyl (Trimethylsilyl)allylation from the Alcohol or Aldehyde Oxidation Level},
journal = {Journal of the American Chemical Society},
year = {2010},
volume = {132},
publisher = {American Chemical Society (ACS)},
month = {jun},
url = {https://doi.org/10.1021/ja103299f},
number = {26},
pages = {9153--9156},
doi = {10.1021/ja103299f}
}
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MLA
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Han, Soo Bong, et al. “Iridium-Catalyzed anti-Diastereo- and Enantioselective Carbonyl (Trimethylsilyl)allylation from the Alcohol or Aldehyde Oxidation Level.” Journal of the American Chemical Society, vol. 132, no. 26, Jun. 2010, pp. 9153-9156. https://doi.org/10.1021/ja103299f.