Journal of the American Chemical Society, volume 138, issue 17, pages 5467-5478
Enantioselective Alcohol C–H Functionalization for Polyketide Construction: Unlocking Redox-Economy and Site-Selectivity for Ideal Chemical Synthesis
Publication type: Journal Article
Publication date: 2016-04-26
Quartile SCImago
Q1
Quartile WOS
Q1
Impact factor: 15
ISSN: 00027863, 15205126
General Chemistry
Catalysis
Biochemistry
Colloid and Surface Chemistry
Abstract
The development and application of stereoselective and site-selective catalytic methods that directly convert lower alcohols to higher alcohols are described. These processes merge the characteristics of transfer hydrogenation and carbonyl addition, exploiting alcohols and π-unsaturated reactants as redox pairs, which upon hydrogen transfer generate transient carbonyl-organometal pairs en route to products of C-C coupling. Unlike classical carbonyl additions, stoichiometric organometallic reagents and discrete alcohol-to-carbonyl redox reactions are not required. Additionally, due to a kinetic preference for primary alcohol dehydrogenation, the site-selective modification of glycols and higher polyols is possible, streamlining or eliminating use of protecting groups. The total syntheses of several iconic type I polyketide natural products were undertaken using these methods. In each case, the target compounds were prepared in significantly fewer steps than previously achieved.
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1 publication, 0.69%
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Citations by publishers
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70
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Wiley
62 publications, 42.76%
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American Chemical Society (ACS)
49 publications, 33.79%
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Royal Society of Chemistry (RSC)
13 publications, 8.97%
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Springer Nature
7 publications, 4.83%
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Elsevier
5 publications, 3.45%
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Multidisciplinary Digital Publishing Institute (MDPI)
2 publications, 1.38%
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Society of Synthetic Organic Chemistry
2 publications, 1.38%
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American Association for the Advancement of Science (AAAS)
1 publication, 0.69%
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Autonomous Non-profit Organization Editorial Board of the journal Uspekhi Khimii
1 publication, 0.69%
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70
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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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Feng J., Kasun Z. A., Krische M. J. Enantioselective Alcohol C–H Functionalization for Polyketide Construction: Unlocking Redox-Economy and Site-Selectivity for Ideal Chemical Synthesis // Journal of the American Chemical Society. 2016. Vol. 138. No. 17. pp. 5467-5478.
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Feng J., Kasun Z. A., Krische M. J. Enantioselective Alcohol C–H Functionalization for Polyketide Construction: Unlocking Redox-Economy and Site-Selectivity for Ideal Chemical Synthesis // Journal of the American Chemical Society. 2016. Vol. 138. No. 17. pp. 5467-5478.
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TY - JOUR
DO - 10.1021/jacs.6b02019
UR - https://doi.org/10.1021/jacs.6b02019
TI - Enantioselective Alcohol C–H Functionalization for Polyketide Construction: Unlocking Redox-Economy and Site-Selectivity for Ideal Chemical Synthesis
T2 - Journal of the American Chemical Society
AU - Feng, Jiajie
AU - Kasun, Zachary A
AU - Krische, Michael J
PY - 2016
DA - 2016/04/26 00:00:00
PB - American Chemical Society (ACS)
SP - 5467-5478
IS - 17
VL - 138
SN - 0002-7863
SN - 1520-5126
ER -
Cite this
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@article{2016_Feng,
author = {Jiajie Feng and Zachary A Kasun and Michael J Krische},
title = {Enantioselective Alcohol C–H Functionalization for Polyketide Construction: Unlocking Redox-Economy and Site-Selectivity for Ideal Chemical Synthesis},
journal = {Journal of the American Chemical Society},
year = {2016},
volume = {138},
publisher = {American Chemical Society (ACS)},
month = {apr},
url = {https://doi.org/10.1021/jacs.6b02019},
number = {17},
pages = {5467--5478},
doi = {10.1021/jacs.6b02019}
}
Cite this
MLA
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Feng, Jiajie, et al. “Enantioselective Alcohol C–H Functionalization for Polyketide Construction: Unlocking Redox-Economy and Site-Selectivity for Ideal Chemical Synthesis.” Journal of the American Chemical Society, vol. 138, no. 17, Apr. 2016, pp. 5467-5478. https://doi.org/10.1021/jacs.6b02019.