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

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

Deadline for manuscript submissions: closed (15 March 2004)

Special Issue Editors

Guest Editor
Dr. Margarita Parra-Alvarez

Department of Organic Chemistry, Faculty of Chemistry, University of Valencia, 46100 Burjassot, Spain
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Interests: reactivity; regioselectivity; enantioselectivity; enediolates and dienediolates of carboxylic acids; chemosensors; chemical warfare; explosives; optical detection; fluorescence
Guest Editor
Dr. Salvador Gil

Department of Organic Chemistry Ed. Investigación Faculty of Chemistry University of Valencia Dr. Moliner, 50 46100-Burjassot (Valencia)
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Published Papers (10 papers)

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Editorial

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Open AccessEditorial Carbanion Chemistry from Carboxylic Acids: a Special Issue in Honor of Professor Ramón Mestres on his 65th Birthday.
Molecules 2004, 9(5), 264-265; doi:10.3390/90500264
Received: 23 February 2004 / Accepted: 1 March 2004 / Published: 30 April 2004
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Research

Jump to: Editorial

Open AccessArticle Investigations into the Use of a Polyfluorooctanol as an Auxiliary Component for an Aldol Reaction
Molecules 2004, 9(5), 266-277; doi:10.3390/90500266
Received: 19 January 2004 / Revised: 19 February 2004 / Accepted: 12 March 2004 / Published: 30 April 2004
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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
Open AccessArticle Self-assembly of [2]Rotaxane Exploiting Reversible Pt(II)- Pyridine Coordinate Bonds
Molecules 2004, 9(5), 278-286; doi:10.3390/90500278
Received: 22 January 2004 / Accepted: 25 January 2004 / Published: 30 April 2004
Cited by 7 | PDF Full-text (268 KB) | HTML Full-text | XML Full-text
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
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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
Open AccessArticle Synthesis of Highly Functionalised Enantiopure Bicyclo[3.2.1]- octane Systems from Carvone
Molecules 2004, 9(5), 287-299; doi:10.3390/90500287
Received: 2 February 2004 / Accepted: 8 March 2004 / Published: 30 April 2004
Cited by 8 | PDF Full-text (229 KB) | HTML Full-text | XML Full-text
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
Open AccessArticle From Labdanes to Drimanes. Degradation of the Side Chain of Dihydrozamoranic Acid.
Molecules 2004, 9(5), 300-322; doi:10.3390/90500300
Received: 23 February 2004 / Revised: 4 March 2004 / Accepted: 5 March 2004 / Published: 30 April 2004
Cited by 3 | PDF Full-text (283 KB) | HTML Full-text | XML Full-text
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
Open AccessArticle 1-Hydroxymethyl-4-phenylsulfonybutadiene, a Versatile Building Block for the Synthesis of 2,3,4-Trisusbtituted Tetrahydrothiophenes
Molecules 2004, 9(5), 323-329; doi:10.3390/90500323
Received: 24 February 2004 / Revised: 4 March 2004 / Accepted: 10 March 2004 / Published: 30 April 2004
Cited by 3 | PDF Full-text (166 KB) | HTML Full-text | XML Full-text
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
Open AccessArticle Masked ω-Lithio Ester Enolates: Synthetic Applications
Molecules 2004, 9(5), 330-348; doi:10.3390/90500330
Received: 25 February 2004 / Accepted: 15 March 2004 / Published: 30 April 2004
Cited by 7 | PDF Full-text (235 KB) | HTML Full-text | XML Full-text
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
Open AccessArticle Polymer-Supported Cinchona Alkaloid-Derived Ammonium Salts as Recoverable Phase-Transfer Catalysts for the Asymmetric Synthesis of α-Amino Acids
Molecules 2004, 9(5), 349-364; doi:10.3390/90500349
Received: 2 March 2004 / Accepted: 22 March 2004 / Published: 30 April 2004
Cited by 25 | PDF Full-text (219 KB) | HTML Full-text | XML Full-text
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
Open AccessArticle Nucleophilic Benzoylation Using a Mandelic Acid Dioxolanone as a Synthetic Equivalent of the Benzoyl Carbanion. Oxidative Decarboxylation of α-Hydroxyacids
Molecules 2004, 9(5), 365-372; doi:10.3390/90500365
Received: 5 March 2004 / Accepted: 18 March 2004 / Published: 30 April 2004
Cited by 4 | PDF Full-text (179 KB) | HTML Full-text | XML Full-text
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
Open AccessArticle A Novel Strategy Towards the Asymmetric Synthesis of Orthogonally Funtionalised 2-N-Benzyl-N-α-methylbenzylamino- 5-carboxymethyl-cyclopentane-1-carboxylic acid.
Molecules 2004, 9(5), 373-382; doi:10.3390/90500373
Received: 15 March 2004 / Revised: 24 March 2004 / Accepted: 24 March 2004 / Published: 30 April 2004
Cited by 4 | PDF Full-text (198 KB) | HTML Full-text | XML Full-text
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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