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Carbanion chemistry from Carboxylic acids in honor of Prof. Ramón Mestres on his 65th anniversary

A special issue of Molecules (ISSN 1420-3049).

Deadline for manuscript submissions: closed (15 March 2004) | Viewed by 91993

Special Issue Editors

Instituto Interuniversitario de Reconocimiento Molecular y Desarrollo Tecnológico (IDM), Universitat de València, Doctor Moliner 50, Burjassot, 46100 Valencia, Spain
Interests: gated mesoporous materials; drug delivery; molecular sensing; chromo and fluorogenic chemosensors and probes; molecular recognition
Special Issues, Collections and Topics in MDPI journals
Department of Organic Chemistry, Ed. Investigación Faculty of Chemistry, University of Valencia Dr. Moliner, 50 46100 Burjassot (Valencia), Spain

Published Papers (10 papers)

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Editorial

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126 KiB  
Editorial
Carbanion Chemistry from Carboxylic Acids: a Special Issue in Honor of Professor Ramón Mestres on his 65th Birthday.
by Margarita Parra and Salvador Gil
Molecules 2004, 9(5), 264-265; https://doi.org/10.3390/90500264 - 30 Apr 2004
Cited by 4 | Viewed by 5840
Abstract
This special issue of Molecules is to honour the 65th birthday of Professor Ramón Mestres.[...] Full article

Research

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198 KiB  
Article
A Novel Strategy Towards the Asymmetric Synthesis of Orthogonally Funtionalised 2-N-Benzyl-N-α-methylbenzylamino- 5-carboxymethyl-cyclopentane-1-carboxylic acid.
by Narciso M. Garrido, Mohamed M. El Hammoumi, David Díez, Mercedes García and Julio G. Urones
Molecules 2004, 9(5), 373-382; https://doi.org/10.3390/90500373 - 30 Apr 2004
Cited by 8 | Viewed by 9800
Abstract
The asymmetric synthesis of the orthogonally funtionalised compounds tert-butyl 2-N-benzyl-N-α-methylbenzylamino-5-methoxycarbonylmethylcyclopentane- 1-carboxylate and methyl 2-N-benzyl-N-α-methylbenzylamino-5–carboxymethylcyclo- pentane-1-carboxylate by a domino reaction of tert-butyl methyl (E,E)-octa-2,6- diendioate with lithium N-α-methylbenzyl-N-benzylamide initiated by a Michael addition, subsequent 5-exo-trig intramolecular cyclisation and posterior selective hydrolysis with trifluoroacetic acid [...] Read more.
The asymmetric synthesis of the orthogonally funtionalised compounds tert-butyl 2-N-benzyl-N-α-methylbenzylamino-5-methoxycarbonylmethylcyclopentane- 1-carboxylate and methyl 2-N-benzyl-N-α-methylbenzylamino-5–carboxymethylcyclo- pentane-1-carboxylate by a domino reaction of tert-butyl methyl (E,E)-octa-2,6- diendioate with lithium N-α-methylbenzyl-N-benzylamide initiated by a Michael addition, subsequent 5-exo-trig intramolecular cyclisation and posterior selective hydrolysis with trifluoroacetic acid is reported. Full article
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179 KiB  
Article
Nucleophilic Benzoylation Using a Mandelic Acid Dioxolanone as a Synthetic Equivalent of the Benzoyl Carbanion. Oxidative Decarboxylation of α-Hydroxyacids
by Gonzalo Blay, Isabel Fernández, Belén Monje and José R. Pedro
Molecules 2004, 9(5), 365-372; https://doi.org/10.3390/90500365 - 30 Apr 2004
Cited by 5 | Viewed by 8931
Abstract
The synthesis of alkyl aryl ketones using a mandelic acid dioxolanone as a synthetic equivalent (Umpolung) of the benzoyl carbanion is reported. The methodology involves alkylation of the mandelic acid dioxolanone, hydrolysis of the dioxolanone moiety in the alkylated products and oxidative decarboxylation [...] Read more.
The synthesis of alkyl aryl ketones using a mandelic acid dioxolanone as a synthetic equivalent (Umpolung) of the benzoyl carbanion is reported. The methodology involves alkylation of the mandelic acid dioxolanone, hydrolysis of the dioxolanone moiety in the alkylated products and oxidative decarboxylation of the resulting α-hydroxyacids. The last step is carried out in a catalytic aerobic way using a Co (III) complex in the presence of pivalaldehyde under very mild conditions. Full article
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219 KiB  
Article
Polymer-Supported Cinchona Alkaloid-Derived Ammonium Salts as Recoverable Phase-Transfer Catalysts for the Asymmetric Synthesis of α-Amino Acids
by Rafael Chinchilla, Patricia Mazón and Carmen Nájera
Molecules 2004, 9(5), 349-364; https://doi.org/10.3390/90500349 - 30 Apr 2004
Cited by 31 | Viewed by 10715
Abstract
Alkaloids such as cinchonidine, quinine and N-methylephedrine have been N-alkylated using polymeric benzyl halides or co-polymerized and then N-alkylated, thus affording a series of polymer-supported chiral ammonium salts which have been employed as phase-transfer catalysts in the asymmetric benzylation of an N-(diphenylmethylene)glycine ester. [...] Read more.
Alkaloids such as cinchonidine, quinine and N-methylephedrine have been N-alkylated using polymeric benzyl halides or co-polymerized and then N-alkylated, thus affording a series of polymer-supported chiral ammonium salts which have been employed as phase-transfer catalysts in the asymmetric benzylation of an N-(diphenylmethylene)glycine ester. These new polymeric catalysts can be easily recovered by simple filtration after the reaction and reused. The best ee’s were achieved when Merrifield resin-anchored cinchonidinium ammonium salts were employed. Full article
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235 KiB  
Article
Masked ω-Lithio Ester Enolates: Synthetic Applications
by Miguel Yus, Rosario Torregrosa and Isidro M. Pastor
Molecules 2004, 9(5), 330-348; https://doi.org/10.3390/90500330 - 30 Apr 2004
Cited by 11 | Viewed by 11320
Abstract
The protocol of lithiation by means of lithium and a catalytic (5% molar) amount of DTBB (4,4’-di-tert-butylbiphenyl), applied to ω-chloro ortho ester 6 under Barbier-type conditions gives, after final acid-catalyzed methanolysis, the corresponding functionalized esters 8 or 9 (for chlorotrimethylsilane as electrophile) or, [...] Read more.
The protocol of lithiation by means of lithium and a catalytic (5% molar) amount of DTBB (4,4’-di-tert-butylbiphenyl), applied to ω-chloro ortho ester 6 under Barbier-type conditions gives, after final acid-catalyzed methanolysis, the corresponding functionalized esters 8 or 9 (for chlorotrimethylsilane as electrophile) or, after ortho ester deprotection and acid catalyzed treatment, the δ-lactones 11. The procedure is also practical for bicyclic ortho esters 14: the β-chloro OBO ester derivate generates the γ- lactones 15 and the γ-chloro OBO ester gives corresponding esters 8. Full article
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166 KiB  
Article
1-Hydroxymethyl-4-phenylsulfonybutadiene, a Versatile Building Block for the Synthesis of 2,3,4-Trisusbtituted Tetrahydrothiophenes
by David Díez, M. Templo Benéitez, Isidro S. Marcos, N. M. Garrido, P. Basabe and Julio G. Urones
Molecules 2004, 9(5), 323-329; https://doi.org/10.3390/90500323 - 30 Apr 2004
Cited by 3 | Viewed by 7775
Abstract
A method to synthesize chiral 2,3,4-trisusbtituted tetrahydrothiophenes in both enantiomerically pure forms starting from 1-hydroxymethyl-4-phenylsulfonylbutadiene is described. Full article
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283 KiB  
Article
From Labdanes to Drimanes. Degradation of the Side Chain of Dihydrozamoranic Acid.
by Jesús M.L. Rodilla, D. Díez, J. G. Urones and Pedro M. Rocha
Molecules 2004, 9(5), 300-322; https://doi.org/10.3390/90500300 - 30 Apr 2004
Cited by 3 | Viewed by 9186
Abstract
A new route for the degradation of the saturated side chain of dihydrozamoranic acid has been devised, giving an advanced intermediate, compound 14, useful for the synthesis of insect antifeedants such as warburganal and polygodial. Full article
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229 KiB  
Article
Synthesis of Highly Functionalised Enantiopure Bicyclo[3.2.1]- octane Systems from Carvone
by Antonio Abad, Consuelo Agulló, Ana C. Cuñat, Ignacio De Alfonso, Ismael Navarro and Noelia Vera
Molecules 2004, 9(5), 287-299; https://doi.org/10.3390/90500287 - 30 Apr 2004
Cited by 15 | Viewed by 11557
Abstract
The commercially available monoterpene carvone has been efficiently convertedinto the tricyclo[3.2.1.02.7]octane and bicyclo[3.2.1]octane systems characteristic of somebiologically active compounds. The sequence used for this transformation involves as keyfeatures an intramolecular Diels-Alder reaction of a 5-vinyl-1,3-cyclohexadiene and acyclopropane ring opening. Full article
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268 KiB  
Article
Self-assembly of [2]Rotaxane Exploiting Reversible Pt(II)- Pyridine Coordinate Bonds
by Pablo Ballester, Magdalena Capó, Antoni Costa, Pere M. Deyà, Antoni Frontera and Rosa M. Gomila
Molecules 2004, 9(5), 278-286; https://doi.org/10.3390/90500278 - 30 Apr 2004
Cited by 8 | Viewed by 8015
Abstract
A dinuclear self-assembled cationic macrocycle based on Pt(II)-N(pyridine) coordinative bonds and having competitive triflate anions, as metal counterions, is used in the construction of [2]rotaxane and [2]pseudorotaxane architectures assisted by hydrogen bonding. The kinetic lability of the Pt(II)-N(pyridine) coordinative bond controls the dynamics [...] Read more.
A dinuclear self-assembled cationic macrocycle based on Pt(II)-N(pyridine) coordinative bonds and having competitive triflate anions, as metal counterions, is used in the construction of [2]rotaxane and [2]pseudorotaxane architectures assisted by hydrogen bonding. The kinetic lability of the Pt(II)-N(pyridine) coordinative bond controls the dynamics of the [2]rotaxane. Full article
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205 KiB  
Article
Investigations into the Use of a Polyfluorooctanol as an Auxiliary Component for an Aldol Reaction
by Jason Eames and Hasina Khanom
Molecules 2004, 9(5), 266-277; https://doi.org/10.3390/90500266 - 30 Apr 2004
Cited by 4 | Viewed by 8176
Abstract
Results are reported on the efficiency of polyfluorooctanol as a perfluorousauxiliary component in the aldol reaction between the enolate derived frompolyfluorooctyl acetate and 2-fluorobenzaldehyde. Reduction of the correspondingpolyfluoro β-hydroxy ester with Super Hydride® gave the required 1,3-diol in good yield. Full article
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