Resolution of Carboxylic Acids Using Copper(I)-Promoted Removal of Propargylic Esters under Neutral ConditionsClick to copy article linkArticle link copied!
Abstract

A method for the optical resolution of carboxylic acids is described. Condensation of racemic carboxylic acids with chiral terminal propargyl alcohols gave separable diastereomeric esters. Chromatographic separation followed by heating the individual diastereomers in methanol with catalytic copper(I) halide regenerated the carboxylic acids in good yields and in enantiomeric ratios of ≥94%. This method is particularly useful for the resolution of carboxylic acids that are incompatible with conventional ester hydrolysis.
Cited By
Smart citations by scite.ai include citation statements extracted from the full text of the citing article. The number of the statements may be higher than the number of citations provided by ACS Publications if one paper cites another multiple times or lower if scite has not yet processed some of the citing articles.
This article is cited by 12 publications.
- Laura M. Bohn and Jeffrey Aubé . Seeking (and Finding) Biased Ligands of the Kappa Opioid Receptor. ACS Medicinal Chemistry Letters 2017, 8
(7)
, 694-700. https://doi.org/10.1021/acsmedchemlett.7b00224
- Emilis Gudelis, Aurimas Bieliauskas, Rūta Gruškienė, Vytas Martynaitis, Neringa Kleizienė, Frank A. Sløk, Algirdas Šačkus. Synthesis of chiral 2-(N-Boc-azetidin-3-yl)-2-alkylpropanoic acids as novel GABA derivatives. Monatshefte für Chemie - Chemical Monthly 2024, 155
(1)
, 83-97. https://doi.org/10.1007/s00706-023-03149-1
- Hao Tian, Yan He, Shaojin Liu, Zhikun Yang, Jine Wang, Jianmin Li, Jianjun Zhang, Liusheng Duan, Zhaohu Li, Weiming Tan. Improved synthetic route of
exo
‐16,17‐dihydro‐gibberellin A5‐13‐acetate and the bioactivity of its derivatives towards
Arabidopsis thaliana. Pest Management Science 2020, 76
(2)
, 807-817. https://doi.org/10.1002/ps.5584
- Luxi Qiao, Emily Fisher, Lindsay McMurray, Selena Milicevic Sephton, Matthew Hird, Nisha Kuzhuppilly‐Ramakrishnan, David J. Williamson, Xiouyun Zhou, Eryn Werry, Michael Kassiou, Saijinder Luthra, William Trigg, Franklin I. Aigbirhio. Radiosynthesis of (
R
,
S
)‐[
18
F]GE387: A Potential PET Radiotracer for Imaging Translocator Protein 18 kDa (TSPO) with Low Binding Sensitivity to the Human Gene Polymorphism rs6971. ChemMedChem 2019, 14
(9)
, 982-993. https://doi.org/10.1002/cmdc.201900023
- Hao Tian, Yiren Xu, Shaojin Liu, Dingsha Jin, Jianjun Zhang, Liusheng Duan, Weiming Tan. Synthesis of Gibberellic Acid Derivatives and Their Effects on Plant Growth. Molecules 2017, 22
(5)
, 694. https://doi.org/10.3390/molecules22050694
- Tse‐Lok Ho, Mary Fieser, Louis Fieser, Rick Danheiser, William Roush, Janice Smith. Copper(
I
) Chloride. 2017https://doi.org/10.1002/9780471264194.fos02876.pub6
- Tse‐Lok Ho, Mary Fieser, Louis Fieser, Rick Danheiser, William Roush, Janice Smith. Copper(
I
) Chloride. 2017https://doi.org/10.1002/9780471264194.fos02876.pub7
- Tse‐Lok Ho, Mary Fieser, Louis Fieser, Rick Danheiser, William Roush, Janice Smith. Copper(
I
) Chloride. 2013, 225-227. https://doi.org/10.1002/9780471264194.fos02876
- Tse‐Lok Ho, Mary Fieser, Louis Fieser, Rick Danheiser, William Roush, Janice Smith. Copper(
I
) Chloride. 2013, 225-227. https://doi.org/10.1002/9780471264194.fos02876.pub5
- Robert E. Gawley, Jeffrey Aubé. Practical Aspects of Asymmetric Synthesis. 2012, 63-95. https://doi.org/10.1016/B978-0-08-044860-2.00002-7
- Di-Han Zhang, Zhen Zhang, Min Shi. Transition metal-catalyzed carbocyclization of nitrogen and oxygen-tethered 1,n-enynes and diynes: synthesis of five or six-membered heterocyclic compounds. Chemical Communications 2012, 48
(83)
, 10271. https://doi.org/10.1039/c2cc34739c
- Partha Ghosh, Jeffrey Aube. ChemInform Abstract: Resolution of Carboxylic Acids Using Copper(I)‐Promoted Removal of Propargylic Esters under Neutral Conditions.. ChemInform 2011, 42
(33)
https://doi.org/10.1002/chin.201133021
Article Views are the COUNTER-compliant sum of full text article downloads since November 2008 (both PDF and HTML) across all institutions and individuals. These metrics are regularly updated to reflect usage leading up to the last few days.
Citations are the number of other articles citing this article, calculated by Crossref and updated daily. Find more information about Crossref citation counts.
The Altmetric Attention Score is a quantitative measure of the attention that a research article has received online. Clicking on the donut icon will load a page at altmetric.com with additional details about the score and the social media presence for the given article. Find more information on the Altmetric Attention Score and how the score is calculated.