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Literature DB >> 18998679

Catalytic enantioselective Meerwein-Eschenmoser Claisen rearrangement: asymmetric synthesis of allyl oxindoles.

Elizabeth C Linton¹, Marisa C Kozlowski.

Abstract

The first catalytic, enantioselective Meerwein-Eschenmoser Claisen rearrangement has been achieved. Palladium(II) BINAP or phosphinooxazoline catalysts were employed to generate oxindole products with 100% conversion and up to 92% ee.

Entities: Chemical

Year: 2008 PMID： 18998679 DOI： 10.1021/ja807026z

Source DB: PubMed Journal: J Am Chem Soc ISSN： 0002-7863 Impact factor: 15.419

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Cited

34 in total

1. The palladium catalyzed asymmetric addition of oxindoles and allenes: an atom-economical versatile method for the construction of chiral indole alkaloids.

Authors: Barry M Trost; Jia Xie; Joshua D Sieber
Journal: J Am Chem Soc Date: 2011-11-30 Impact factor: 15.419

2. Alpha-arylation of 3-aryloxindoles.

Authors: Cheng-Kang Mai; Matthew F Sammons; Tarek Sammakia
Journal: Org Lett Date: 2010-05-21 Impact factor: 6.005

3. Rapid synthesis of an electron-deficient t-BuPHOX ligand: cross-coupling of aryl bromides with secondary phosphine oxides.

Authors: Nolan T McDougal; Jan Streuff; Herschel Mukherjee; Scott C Virgil; Brian M Stoltz
Journal: Tetrahedron Lett Date: 2010-10-20 Impact factor: 2.415

4. Asymmetric Pd-Catalyzed Alkene Carboamination Reactions for the Synthesis of 2-Aminoindane Derivatives.

Authors: Derick R White; Johnathon T Hutt; John P Wolfe
Journal: J Am Chem Soc Date: 2015-08-27 Impact factor: 15.419

5. Asymmetric synthesis of allenyl oxindoles and spirooxindoles by a catalytic enantioselective Saucy-Marbet Claisen rearrangement.

Authors: Trung Cao; Joshua Deitch; Elizabeth C Linton; Marisa C Kozlowski
Journal: Angew Chem Int Ed Engl Date: 2012-01-27 Impact factor: 15.336

Catalytic enantioselective Meerwein-Eschenmoser Claisen rearrangement: asymmetric synthesis of allyl oxindoles.

1. The palladium catalyzed asymmetric addition of oxindoles and allenes: an atom-economical versatile method for the construction of chiral indole alkaloids.

2. Alpha-arylation of 3-aryloxindoles.

3. Rapid synthesis of an electron-deficient t-BuPHOX ligand: cross-coupling of aryl bromides with secondary phosphine oxides.

4. Asymmetric Pd-Catalyzed Alkene Carboamination Reactions for the Synthesis of 2-Aminoindane Derivatives.

5. Asymmetric synthesis of allenyl oxindoles and spirooxindoles by a catalytic enantioselective Saucy-Marbet Claisen rearrangement.

6. A General and Practical Palladium-Catalyzed Direct α-Arylation of Amides with Aryl Halides.

7. A density functional theory approach toward substituent effect in Meerwein-Eschenmoser-Claisen rearrangement.

8. Further Developments and Applications of Oxazoline-Containing Ligands in Asymmetric Catalysis.

9. Design of a bisamidinium claisen rearrangement catalyst for monodentate substrates.

10. Catalytic double stereoinduction in asymmetric allylic alkylation of oxindoles.