Thallium(III) in Organic Synthesis

Synthesis
DOI: 10.1055/s-0029-1218669



Abstract

This review article discusses the literature regarding thallium(III) compounds in synthetic organic chemistry published in the last decade, including several applications in the total synthesis of natural products. The reactions that received the most attention in this period were: i) the oxidative rearrangement of chalcones; ii) the ring contraction of cyclic alkenes; iii) the oxidation of homoallylic alcohols; iv) aromatic thallations; and v) oxidative couplings, including with phenols.
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© Georg Thieme Verlag Stuttgart ˙ New York

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A Simple, Advantageous Synthesis of 5-Substituted 1H-Tetrazoles

Synlett null; null: e3-e3
DOI: 10.1055/s-0029-1219366



© Georg Thieme Verlag Stuttgart ˙ New York

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SYNFORM ISSUE 2010/02

Synlett null; null: A11-A21
DOI: 10.1055/s-0029-1219368



© Georg Thieme Verlag, Rüdigerstr. 14, 70469 Stuttgart, Germany. All rights reserved. This journal, including all individual contributions and illustrations published therein, is legally protected by copyright for the duration of the copyright period. Any use, exploitation or commercialization outside the narrow limits set by copyright legislation, without the publisher's consent, is illegal and liable to criminal prosecution. This applies in particular to photostat reproduction, copying, cyclostyling, mimeographing or duplication of any kind, translating, preparation of microfilms, and electronic data processing and storage.

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Carbon-Carbon Double-Bond Isomerization and Diels-Alder Reaction of [nl]Dimethyl 5-Methylene-4-isopropylidene-2-cycloheptene-1,1-dicarboxylate with Dienophiles

Synlett null; null: e2-e2
DOI: 10.1055/s-0029-1219193



© Georg Thieme Verlag Stuttgart ˙ New York

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Fluorous Mixture Synthesis of Four Stereoisomers of the C21-C40 Fragment of Tetrafibricin

Synlett
DOI: 10.1055/s-0029-1219376



Abstract

Four stereoisomers of the C21-C40 fragment are synthesized in a single exercise with the aid of fluorous tagging to encode configurations at C37 and C33. After demixing and detagging, the isomers were found to have substantially identical H NMR spectra. However, there were some small but reliable differences in their C NMR spectra.
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© Georg Thieme Verlag Stuttgart ˙ New York

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(1R,5R)-1-(1′-Dimethylaminoethyl)-2-isopropylidene-5-methylcyclohexanol as a Chiral Ligand in the Enantioselective Addition of Diethylzinc to Aldehydes

Synlett
DOI: 10.1055/s-0029-1219379



Abstract

An efficient chiral ligand, (1,5)-1-(1′-dimethylaminoethyl)-2-isopropylidene-5-methylcyclohexanol, has been developed for the enantioselective addition of diethylzinc to some prochiral aldehydes to afford -alcohols. The overall conversion rate was 80-98% with excellent enantiomeric excess (79-98%).
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© Georg Thieme Verlag Stuttgart ˙ New York

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Methodology for the Synthesis of Substituted 1,3-Oxazoles

Synlett
DOI: 10.1055/s-0029-1219374



Abstract

The halogen dance isomerization is a facile and preparatively effective pathway for the synthesis of 2,4,5-trisubstituted 1,3-oxazoles.
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© Georg Thieme Verlag Stuttgart ˙ New York

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Asymmetric Conjugate Addition of Crotylstannane: Synthesis of (-)-Lasiol

Synlett
DOI: 10.1055/s-0029-1219381



Abstract

Lasiol, the major component of the mandibular gland secretion, serves as the primary sex attractant of the male ant, . Our interest in lasiol stems from the stereochemistry of the chiral methyl substituents and the synthetic challenges posed by this common structural motif. As such, an asymmetric 1,4-conjugate addition of an allylic stannane to produce the 1,2--dimethyl arrangement with high stereocontrol has resulted in the synthesis of (-)-lasiol.
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© Georg Thieme Verlag Stuttgart ˙ New York

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Thieme Chemistry Journal Awardees – Where Are They Now? Bifunctional Organocatalysis with N-Formyl-l-Proline: A Novel Approach to Epoxide Ring Opening and Sulfide Oxidation

Synlett
DOI: 10.1055/s-0029-1219363



Abstract

A conceptually distinct approach to the aminolysis of 1,2-epoxides, which involves Lewis base-Brønsted acid catalysis employing -formyl--proline as an easily accessible bifunctional organocatalyst and water as a solvent is presented. The potential of -formyl--proline as organocatalyst for the sulfide oxidation reaction using aqueous hydrogen peroxide as environmentally benign and readily available oxidant is also demonstrated. Good to high yields are achieved for both reactions.
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© Georg Thieme Verlag Stuttgart ˙ New York

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First Site-Selective Suzuki-Miyaura Reactions of 2,3,4-Tribromothiophene

Synlett
DOI: 10.1055/s-0029-1219380



Abstract

The first Suzuki-Miyaura reactions of 2,3,4-tribromothiophene are reported. These reactions provide a convenient and site-selective approach to 2-aryl-3,4-dibromothiophenes, 2,4-diaryl-3-bromothiophenes, and 2,3,4-triarylthiophenes.
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© Georg Thieme Verlag Stuttgart ˙ New York

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