Journal of the American Chemical Society, volume 144, issue 19, pages 8861-8869
Stereo- and Site-Selective Conversion of Primary Alcohols to Allylic Alcohols via Ruthenium-Catalyzed Hydrogen Auto-Transfer Mediated by 2-Butyne
Publication type: Journal Article
Publication date: 2022-05-03
Quartile SCImago
Q1
Quartile WOS
Q1
Impact factor: 15
ISSN: 00027863, 15205126
General Chemistry
Catalysis
Biochemistry
Colloid and Surface Chemistry
Abstract
The first enantioselective ruthenium-catalyzed carbonyl vinylations via hydrogen autotransfer are described. Using a ruthenium-JOSIPHOS catalyst, primary alcohols 2a-2m and 2-butyne 1a are converted to chiral allylic alcohols 3a-3m with excellent levels of absolute stereocontrol. Notably, 1°,2°-1,3-diols participate in site-selective C-C coupling, enabling asymmetric carbonyl vinylation beyond premetalated reagents, exogenous reductants, or hydroxyl protecting groups. Using 2-propanol as a reductant, aldehydes dehydro-2a, 2l participate in highly enantioselective 2-butyne-mediated vinylation under otherwise identical reaction conditions. Regio-, stereo-, and site-selective vinylations mediated by 2-pentyne 1b to form adducts 3n, 3o, and epi-3o also are described. The tiglyl alcohol motif obtained upon butyne-mediated vinylation, which is itself found in diverse secondary metabolites, may be converted to commonly encountered polyketide stereodiads, -triads, and -tetrads, as demonstrated by the formation of adducts 4a-4d. The collective mechanistic studies, including deuterium labeling experiments, corroborate a catalytic cycle involving alcohol dehydrogenation to form a transient aldehyde and a ruthenium hydride, which engages in alkyne hydrometalation to form a nucleophilic vinylruthenium species that enacts carbonyl addition. A stereochemical model for carbonyl addition invoking formyl CH···I[Ru] and CH···O≡C[Ru] hydrogen bonds is proposed based on prior calculations and crystallographic data.
Top-30
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Citations by publishers
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2
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10
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American Chemical Society (ACS)
10 publications, 58.82%
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Wiley
2 publications, 11.76%
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Shanghai Institute of Organic Chemistry
1 publication, 5.88%
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Thieme
1 publication, 5.88%
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Royal Society of Chemistry (RSC)
1 publication, 5.88%
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Autonomous Non-profit Organization Editorial Board of the journal Uspekhi Khimii
1 publication, 5.88%
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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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Ortiz E. et al. Stereo- and Site-Selective Conversion of Primary Alcohols to Allylic Alcohols via Ruthenium-Catalyzed Hydrogen Auto-Transfer Mediated by 2-Butyne // Journal of the American Chemical Society. 2022. Vol. 144. No. 19. pp. 8861-8869.
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Ortiz E., Chang Yu. H., Shezaf J., Shen W., Krische M. J. Stereo- and Site-Selective Conversion of Primary Alcohols to Allylic Alcohols via Ruthenium-Catalyzed Hydrogen Auto-Transfer Mediated by 2-Butyne // Journal of the American Chemical Society. 2022. Vol. 144. No. 19. pp. 8861-8869.
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TY - JOUR
DO - 10.1021/jacs.2c03614
UR - https://doi.org/10.1021/jacs.2c03614
TI - Stereo- and Site-Selective Conversion of Primary Alcohols to Allylic Alcohols via Ruthenium-Catalyzed Hydrogen Auto-Transfer Mediated by 2-Butyne
T2 - Journal of the American Chemical Society
AU - Ortiz, Eliezer
AU - Chang, Yu Hsiang
AU - Shezaf, Jonathan
AU - Shen, Weijia
AU - Krische, Michael J
PY - 2022
DA - 2022/05/03 00:00:00
PB - American Chemical Society (ACS)
SP - 8861-8869
IS - 19
VL - 144
SN - 0002-7863
SN - 1520-5126
ER -
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@article{2022_Ortiz,
author = {Eliezer Ortiz and Yu Hsiang Chang and Jonathan Shezaf and Weijia Shen and Michael J Krische},
title = {Stereo- and Site-Selective Conversion of Primary Alcohols to Allylic Alcohols via Ruthenium-Catalyzed Hydrogen Auto-Transfer Mediated by 2-Butyne},
journal = {Journal of the American Chemical Society},
year = {2022},
volume = {144},
publisher = {American Chemical Society (ACS)},
month = {may},
url = {https://doi.org/10.1021/jacs.2c03614},
number = {19},
pages = {8861--8869},
doi = {10.1021/jacs.2c03614}
}
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Ortiz, Eliezer, et al. “Stereo- and Site-Selective Conversion of Primary Alcohols to Allylic Alcohols via Ruthenium-Catalyzed Hydrogen Auto-Transfer Mediated by 2-Butyne.” Journal of the American Chemical Society, vol. 144, no. 19, May. 2022, pp. 8861-8869. https://doi.org/10.1021/jacs.2c03614.