ACS Catalysis, volume 13, issue 3, pages 1662-1668
Asymmetric Ruthenium-Catalyzed Carbonyl Allylations by Gaseous Allene via Hydrogen Auto-Transfer: 1° versus 2° Alcohol Dehydrogenation for Streamlined Polyketide Construction
Publication type: Journal Article
Publication date: 2023-01-12
Journal:
ACS Catalysis
Quartile SCImago
Q1
Quartile WOS
Q1
Impact factor: 12.9
ISSN: 21555435, 21555435
General Chemistry
Catalysis
Abstract
Iodide-bound ruthenium–JOSIPHOS complexes catalyze the redox-neutral C–C coupling of primary alcohols 2a–2r with the gaseous allene (propadiene) 1a to form enantiomerically enriched homoallylic alcohols 3a–3r with complete atom efficiency. Using formic acid as the reductant, aldehydes dehydro-2a and dehydro-2c participate in reductive C–C coupling with allene to deliver adducts 3a and 3c with comparable levels of asymmetric induction. Deuterium labeling studies corroborate a mechanism in which alcohol dehydrogenation triggers allene hydroruthenation to form transient allylruthenium–aldehyde pairs that participate in carbonyl addition. Notably, due to a kinetic preference for primary alcohol dehydrogenation, chemoselective C–C coupling of 1°,2°-1,3-diols occurs in the absence of protecting groups. As illustrated by the synthesis of C7–C15 of spirastrellolide B and F (7 vs 17 steps), C3–C10 of cryptocarya diacetate (three vs seven or nine steps) and a fragment common to C8′–C14′ of mycolactone F (one vs four steps) and C22–C28 marinomycin A (one vs nine steps), this capability streamlines type I polyketide construction.
Top-30
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Angewandte Chemie
2 publications, 22.22%
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Angewandte Chemie - International Edition
2 publications, 22.22%
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ACS Catalysis
1 publication, 11.11%
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ChemistrySelect
1 publication, 11.11%
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Journal of the American Chemical Society
1 publication, 11.11%
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Chemical Reviews
1 publication, 11.11%
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Russian Chemical Reviews
1 publication, 11.11%
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Citations by publishers
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5
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Wiley
5 publications, 55.56%
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American Chemical Society (ACS)
3 publications, 33.33%
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Autonomous Non-profit Organization Editorial Board of the journal Uspekhi Khimii
1 publication, 11.11%
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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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Saludares C. et al. Asymmetric Ruthenium-Catalyzed Carbonyl Allylations by Gaseous Allene via Hydrogen Auto-Transfer: 1° versus 2° Alcohol Dehydrogenation for Streamlined Polyketide Construction // ACS Catalysis. 2023. Vol. 13. No. 3. pp. 1662-1668.
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Saludares C., Ortiz E., Santana C. G., Spinello B. J., Krische M. J. Asymmetric Ruthenium-Catalyzed Carbonyl Allylations by Gaseous Allene via Hydrogen Auto-Transfer: 1° versus 2° Alcohol Dehydrogenation for Streamlined Polyketide Construction // ACS Catalysis. 2023. Vol. 13. No. 3. pp. 1662-1668.
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TY - JOUR
DO - 10.1021/acscatal.2c05425
UR - https://doi.org/10.1021/acscatal.2c05425
TI - Asymmetric Ruthenium-Catalyzed Carbonyl Allylations by Gaseous Allene via Hydrogen Auto-Transfer: 1° versus 2° Alcohol Dehydrogenation for Streamlined Polyketide Construction
T2 - ACS Catalysis
AU - Saludares, Connor
AU - Ortiz, Eliezer
AU - Santana, Cate G
AU - Spinello, Brian J
AU - Krische, Michael J
PY - 2023
DA - 2023/01/12 00:00:00
PB - American Chemical Society (ACS)
SP - 1662-1668
IS - 3
VL - 13
SN - 2155-5435
SN - 2155-5435
ER -
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@article{2023_Saludares,
author = {Connor Saludares and Eliezer Ortiz and Cate G Santana and Brian J Spinello and Michael J Krische},
title = {Asymmetric Ruthenium-Catalyzed Carbonyl Allylations by Gaseous Allene via Hydrogen Auto-Transfer: 1° versus 2° Alcohol Dehydrogenation for Streamlined Polyketide Construction},
journal = {ACS Catalysis},
year = {2023},
volume = {13},
publisher = {American Chemical Society (ACS)},
month = {jan},
url = {https://doi.org/10.1021/acscatal.2c05425},
number = {3},
pages = {1662--1668},
doi = {10.1021/acscatal.2c05425}
}
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Saludares, Connor, et al. “Asymmetric Ruthenium-Catalyzed Carbonyl Allylations by Gaseous Allene via Hydrogen Auto-Transfer: 1° versus 2° Alcohol Dehydrogenation for Streamlined Polyketide Construction.” ACS Catalysis, vol. 13, no. 3, Jan. 2023, pp. 1662-1668. https://doi.org/10.1021/acscatal.2c05425.