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p. 264-265
Received: 23 February 2004 / Accepted: 1 March 2004 / Published: 30 April 2004
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p. 266-277
Received: 19 January 2004; in revised form: 19 February 2004 / Accepted: 12 March 2004 / Published: 30 April 2004
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| Download PDF Full-text (205 KB) 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.
p. 278-286
Received: 22 January 2004 / Accepted: 25 January 2004 / Published: 30 April 2004
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| Download PDF Full-text (268 KB) 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 of the [2]rotaxane.
p. 287-299
Received: 2 February 2004 / Accepted: 8 March 2004 / Published: 30 April 2004
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| Download PDF Full-text (229 KB) 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.
p. 300-322
Received: 23 February 2004; in revised form: 4 March 2004 / Accepted: 5 March 2004 / Published: 30 April 2004
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| Download PDF Full-text (283 KB) 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.
p. 323-329
Received: 24 February 2004; in revised form: 4 March 2004 / Accepted: 10 March 2004 / Published: 30 April 2004
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| Download PDF Full-text (166 KB) Abstract: A method to synthesize chiral 2,3,4-trisusbtituted tetrahydrothiophenes in both enantiomerically pure forms starting from 1-hydroxymethyl-4-phenylsulfonylbutadiene is described.
p. 330-348
Received: 25 February 2004 / Accepted: 15 March 2004 / Published: 30 April 2004
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| Download PDF Full-text (235 KB) 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, 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.
p. 349-364
Received: 2 March 2004 / Accepted: 22 March 2004 / Published: 30 April 2004
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| Download PDF Full-text (219 KB) 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. 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.
p. 365-372
Received: 5 March 2004 / Accepted: 18 March 2004 / Published: 30 April 2004
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| Download PDF Full-text (179 KB) 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 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.
p. 373-382
Received: 15 March 2004; in revised form: 24 March 2004 / Accepted: 24 March 2004 / Published: 30 April 2004
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| Download PDF Full-text (198 KB) 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 is reported.
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