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Literature DB >> 20738127

Selective synthesis of either isoindole- or isoindoline-1-carboxylic acid esters by Pd(0)-catalyzed enolate arylation.

Abstract

Two efficient palladium-catalyzed intramolecular α-arylation reactions of α-amino acid esters have been developed that allow either 1-isoindolecarboxylic acid esters or the corresponding isoindolines to be selectively synthesized simply by a slight change of reaction conditions.

Entities: Chemical

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Year: 2010 PMID： 20738127 DOI： 10.1021/jo101054j

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

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Cited

5 in total

1. Synthesis of a unique isoindoline/tetrahydroisoquinoline-based tricyclic sultam library utilizing a Heck-aza-Michael strategy.

Authors: Qin Zang; Salim Javed; Patrick Porubsky; Farman Ullah; Benjamin Neuenswander; Gerald H Lushington; Fatima Z Basha; Michael G Organ; Paul R Hanson
Journal: ACS Comb Sci Date: 2012-02-06 Impact factor: 3.784

2. Concise Total Synthesis of (-)-Affinisine Oxindole, (+)-Isoalstonisine, (+)-Alstofoline, (-)-Macrogentine, (+)-N_a -Demethylalstonisine, (-)-Alstonoxine A, and (+)-Alstonisine.

Authors: Michael Rajesh Stephen; M Toufiqur Rahman; V V N Phani Babu Tiruveedhula; German O Fonseca; Jeffrey R Deschamps; James M Cook
Journal: Chemistry Date: 2017-10-18 Impact factor: 5.236

Selective synthesis of either isoindole- or isoindoline-1-carboxylic acid esters by Pd(0)-catalyzed enolate arylation.

1. Synthesis of a unique isoindoline/tetrahydroisoquinoline-based tricyclic sultam library utilizing a Heck-aza-Michael strategy.

2. Concise Total Synthesis of (-)-Affinisine Oxindole, (+)-Isoalstonisine, (+)-Alstofoline, (-)-Macrogentine, (+)-N_a -Demethylalstonisine, (-)-Alstonoxine A, and (+)-Alstonisine.

3. Tandem Cycloisomerization/Suzuki Coupling of Arylethynyl MIDA Boronates.

4. Palladium-catalyzed α-arylation of carbonyls in the de novo synthesis of aromatic heterocycles.

5. Rhodium-catalysed tetradehydro-Diels-Alder reactions of enediynes via a rhodium-stabilized cyclic allene.

Selective synthesis of either isoindole- or isoindoline-1-carboxylic acid esters by Pd(0)-catalyzed enolate arylation.

1. Synthesis of a unique isoindoline/tetrahydroisoquinoline-based tricyclic sultam library utilizing a Heck-aza-Michael strategy.

2. Concise Total Synthesis of (-)-Affinisine Oxindole, (+)-Isoalstonisine, (+)-Alstofoline, (-)-Macrogentine, (+)-Na -Demethylalstonisine, (-)-Alstonoxine A, and (+)-Alstonisine.

3. Tandem Cycloisomerization/Suzuki Coupling of Arylethynyl MIDA Boronates.

4. Palladium-catalyzed α-arylation of carbonyls in the de novo synthesis of aromatic heterocycles.

5. Rhodium-catalysed tetradehydro-Diels-Alder reactions of enediynes via a rhodium-stabilized cyclic allene.

2. Concise Total Synthesis of (-)-Affinisine Oxindole, (+)-Isoalstonisine, (+)-Alstofoline, (-)-Macrogentine, (+)-N_a -Demethylalstonisine, (-)-Alstonoxine A, and (+)-Alstonisine.