Journal of the American Chemical Society, volume 130, issue 20, pages 6340-6341
Enantioselective Iridium-Catalyzed Carbonyl Allylation from the Alcohol or Aldehyde Oxidation Level Using Allyl Acetate as an Allyl Metal Surrogate
Publication type: Journal Article
Publication date: 2008-04-29
Quartile SCImago
Q1
Quartile WOS
Q1
Impact factor: 15
ISSN: 00027863, 15205126
General Chemistry
Catalysis
Biochemistry
Colloid and Surface Chemistry
Abstract
Protocols for highly enantioselective carbonyl allylation from the alcohol or aldehyde oxidation level are described based upon transfer hydrogenative C−C coupling. Exposure of allyl acetate to benzylic alcohols 1a−i in the presence of an iridium catalyst derived from [IrCl(cod)]2 and (R)-BINAP delivers products of C-allylation 2a−i. Employing isopropanol as terminal reductant, exposure of allyl acetate to aryl aldehydes 3a−i in the presence of an iridium catalyst derived from [IrCl(cod)]2 and (−)-TMBTP delivers identical products of C-allylation 2a−i. In all cases examined, exception levels of enantioselectivity are observed. Thus, enantioselective carbonyl allylation is achieved from the alcohol or aldehyde oxidation level in the absence of any preformed allylmetal reagents. These studies define a departure from preformed organometallic reagents in carbonyl additions that transcend the boundaries of oxidation level.
Top-30
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2 publications, 0.91%
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2 publications, 0.91%
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2 publications, 0.91%
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2 publications, 0.91%
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2 publications, 0.91%
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2 publications, 0.91%
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2 publications, 0.91%
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1 publication, 0.46%
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1 publication, 0.46%
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1 publication, 0.46%
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1 publication, 0.46%
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1 publication, 0.46%
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1 publication, 0.46%
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Bulletin of the Korean Chemical Society
1 publication, 0.46%
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Trends in Chemistry
1 publication, 0.46%
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Citations by publishers
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American Chemical Society (ACS)
93 publications, 42.47%
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Wiley
64 publications, 29.22%
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Royal Society of Chemistry (RSC)
22 publications, 10.05%
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Elsevier
13 publications, 5.94%
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Springer Nature
5 publications, 2.28%
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Thieme
3 publications, 1.37%
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Beilstein-Institut
2 publications, 0.91%
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The Chemical Society of Japan
2 publications, 0.91%
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World Scientific
1 publication, 0.46%
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Shanghai Institute of Organic Chemistry
1 publication, 0.46%
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Multidisciplinary Digital Publishing Institute (MDPI)
1 publication, 0.46%
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Frontiers Media S.A.
1 publication, 0.46%
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Oxford University Press
1 publication, 0.46%
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Autonomous Non-profit Organization Editorial Board of the journal Uspekhi Khimii
1 publication, 0.46%
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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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Kim I. S., Ngai M. Yu., Krische M. J. Enantioselective Iridium-Catalyzed Carbonyl Allylation from the Alcohol or Aldehyde Oxidation Level Using Allyl Acetate as an Allyl Metal Surrogate // Journal of the American Chemical Society. 2008. Vol. 130. No. 20. pp. 6340-6341.
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Kim I. S., Ngai M. Yu., Krische M. J. Enantioselective Iridium-Catalyzed Carbonyl Allylation from the Alcohol or Aldehyde Oxidation Level Using Allyl Acetate as an Allyl Metal Surrogate // Journal of the American Chemical Society. 2008. Vol. 130. No. 20. pp. 6340-6341.
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TY - JOUR
DO - 10.1021/ja802001b
UR - https://doi.org/10.1021/ja802001b
TI - Enantioselective Iridium-Catalyzed Carbonyl Allylation from the Alcohol or Aldehyde Oxidation Level Using Allyl Acetate as an Allyl Metal Surrogate
T2 - Journal of the American Chemical Society
AU - Kim, In Su
AU - Ngai, Ming Yu
AU - Krische, Michael J
PY - 2008
DA - 2008/04/29 00:00:00
PB - American Chemical Society (ACS)
SP - 6340-6341
IS - 20
VL - 130
SN - 0002-7863
SN - 1520-5126
ER -
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@article{2008_Kim,
author = {In Su Kim and Ming Yu Ngai and Michael J Krische},
title = {Enantioselective Iridium-Catalyzed Carbonyl Allylation from the Alcohol or Aldehyde Oxidation Level Using Allyl Acetate as an Allyl Metal Surrogate},
journal = {Journal of the American Chemical Society},
year = {2008},
volume = {130},
publisher = {American Chemical Society (ACS)},
month = {apr},
url = {https://doi.org/10.1021/ja802001b},
number = {20},
pages = {6340--6341},
doi = {10.1021/ja802001b}
}
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Kim, In Su, et al. “Enantioselective Iridium-Catalyzed Carbonyl Allylation from the Alcohol or Aldehyde Oxidation Level Using Allyl Acetate as an Allyl Metal Surrogate.” Journal of the American Chemical Society, vol. 130, no. 20, Apr. 2008, pp. 6340-6341. https://doi.org/10.1021/ja802001b.