Journal of the American Chemical Society, volume 133, issue 4, pages 1141-1144
Amplification of Anti-Diastereoselectivity via Curtin−Hammett Effects in Ruthenium-Catalyzed Hydrohydroxyalkylation of 1,1-Disubstituted Allenes: Diastereoselective Formation of All-Carbon Quaternary Centers
Publication type: Journal Article
Publication date: 2010-12-22
Quartile SCImago
Q1
Quartile WOS
Q1
Impact factor: 15
ISSN: 00027863, 15205126
General Chemistry
Catalysis
Biochemistry
Colloid and Surface Chemistry
Abstract
Under the conditions of ruthenium-catalyzed transfer hydrogenation, 1,1-disubstituted allenes 1a-c and alcohols 2a-g engage in redox-triggered generation of allylruthenium-aldehyde pairs to form products of hydrohydroxyalkylation 3a-g, 4a-g, and 5a-g with complete branched regioselectivity. By exploiting Curtin-Hammett effects, good to excellent levels of anti-diastereoselectivity (4:1 to >20:1) are obtained. Thus, all carbon quaternary centers are formed in a diastereoselective fashion upon carbonyl addition from the alcohol oxidation level in the absence of premetalated nucleophiles or stoichiometric byproducts. Exposure of allene 1b to equimolar quantities of alcohol 2a and aldehyde 6b under standard reaction conditions delivers adducts 4a and 4b in a 1:1 ratio. Similarly, exposure of allene 1b to equimolar quantities of aldehyde 6a and alcohol 2b provides adducts 4a and 4b in an identical equimolar ratio. Exposure of allene 1b to d(2)-p-nitrobenzyl alcohol, deuterio-2a, under standard reaction conditions delivers the product of hydrohydroxyalkylation, deuterio-4a, which incorporates deuterium at the carbinol position (>95% (2)H) and the interior vinylic position (34% (2)H). Competition experiments involving exposure of allene 1b to equimolar quantities of benzylic alcohols 2a and deuterio-2a reveal no significant kinetic effect. The collective data corroborate rapid, reversible alcohol dehydrogenation, allene hydrometalation, and (E)-, (Z)-isomerization of the transient allylruthenium in advance of turnover-limiting carbonyl addition. Notably, analogous allene-aldehyde reductive C-C couplings employing 2-propanol as the terminal reductant display poor levels of anti-diastereoselectivity, suggesting that carbonyl addition is not turnover-limiting in reactions conducted from the aldehyde oxidation level.
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Citations by publishers
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5
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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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Zbieg J. R. et al. Amplification of Anti-Diastereoselectivity via Curtin−Hammett Effects in Ruthenium-Catalyzed Hydrohydroxyalkylation of 1,1-Disubstituted Allenes: Diastereoselective Formation of All-Carbon Quaternary Centers // Journal of the American Chemical Society. 2010. Vol. 133. No. 4. pp. 1141-1144.
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Zbieg J. R., Mcinturff E. L., Leung J. C., Krische M. J. Amplification of Anti-Diastereoselectivity via Curtin−Hammett Effects in Ruthenium-Catalyzed Hydrohydroxyalkylation of 1,1-Disubstituted Allenes: Diastereoselective Formation of All-Carbon Quaternary Centers // Journal of the American Chemical Society. 2010. Vol. 133. No. 4. pp. 1141-1144.
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TY - JOUR
DO - 10.1021/ja1104156
UR - https://doi.org/10.1021/ja1104156
TI - Amplification of Anti-Diastereoselectivity via Curtin−Hammett Effects in Ruthenium-Catalyzed Hydrohydroxyalkylation of 1,1-Disubstituted Allenes: Diastereoselective Formation of All-Carbon Quaternary Centers
T2 - Journal of the American Chemical Society
AU - Mcinturff, Emma L
AU - Leung, Joyce C
AU - Zbieg, Jason R
AU - Krische, Michael J
PY - 2010
DA - 2010/12/22 00:00:00
PB - American Chemical Society (ACS)
SP - 1141-1144
IS - 4
VL - 133
SN - 0002-7863
SN - 1520-5126
ER -
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@article{2010_Zbieg,
author = {Emma L Mcinturff and Joyce C Leung and Jason R Zbieg and Michael J Krische},
title = {Amplification of Anti-Diastereoselectivity via Curtin−Hammett Effects in Ruthenium-Catalyzed Hydrohydroxyalkylation of 1,1-Disubstituted Allenes: Diastereoselective Formation of All-Carbon Quaternary Centers},
journal = {Journal of the American Chemical Society},
year = {2010},
volume = {133},
publisher = {American Chemical Society (ACS)},
month = {dec},
url = {https://doi.org/10.1021/ja1104156},
number = {4},
pages = {1141--1144},
doi = {10.1021/ja1104156}
}
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Zbieg, Jason R., et al. “Amplification of Anti-Diastereoselectivity via Curtin−Hammett Effects in Ruthenium-Catalyzed Hydrohydroxyalkylation of 1,1-Disubstituted Allenes: Diastereoselective Formation of All-Carbon Quaternary Centers.” Journal of the American Chemical Society, vol. 133, no. 4, Dec. 2010, pp. 1141-1144. https://doi.org/10.1021/ja1104156.