Literature DB >> 21491889

Resolution of carboxylic acids using copper(I)-promoted removal of propargylic esters under neutral conditions.

Partha Ghosh1, Jeffrey Aubé.   

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.

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Year:  2011        PMID： 21491889      PMCID： PMC3691273          DOI： 10.1021/jo200433w

Source DB:  PubMed          Journal:  J Org Chem        ISSN： 0022-3263            Impact factor:   4.354


  4 in total

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Authors:  Kevin J Frankowski; Partha Ghosh; Vincent Setola; Thuy B Tran; Bryan L Roth; Jeffrey Aubé
Journal:  ACS Med Chem Lett       Date:  2010-08-12       Impact factor: 4.345

2.  Enantioselective copper-catalyzed propargylic amination.

Authors:  Remko J Detz; Mariëlle M E Delville; Henk Hiemstra; Jan H van Maarseveen
Journal:  Angew Chem Int Ed Engl       Date:  2008       Impact factor: 15.336

3.  Synthesis of N-alkyl-octahydroisoquinolin-1-one-8-carboxamide libraries using a tandem Diels-Alder/acylation sequence.

Authors:  Kevin J Frankowski; Erin E Hirt; Yibin Zeng; Ben Neuenswander; Drew Fowler; Frank Schoenen; Jeffrey Aubé
Journal:  J Comb Chem       Date:  2007-09-27

4.  Regioselective oxidative cleavage of benzylidene acetals: synthesis of alpha- and beta-benzoyloxy carboxylic acids.

Authors:  Ponminor Senthil Kumar; Amit Banerjee; Sundarababu Baskaran
Journal:  Angew Chem Int Ed Engl       Date:  2010       Impact factor: 15.336
  4 in total
  3 in total

1.  Seeking (and Finding) Biased Ligands of the Kappa Opioid Receptor.

Authors:  Laura M Bohn; Jeffrey Aubé
Journal:  ACS Med Chem Lett       Date:  2017-07-05       Impact factor: 4.345

2.  Synthesis of Gibberellic Acid Derivatives and Their Effects on Plant Growth.

Authors:  Hao Tian; Yiren Xu; Shaojin Liu; Dingsha Jin; Jianjun Zhang; Liusheng Duan; Weiming Tan
Journal:  Molecules       Date:  2017-04-26       Impact factor: 4.411

3.  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.

Authors:  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
Journal:  ChemMedChem       Date:  2019-04-08       Impact factor: 3.466
  3 in total

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