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Literature DB >> 11418063

Ruthenium(II)-catalyzed cycloaddition of 1,6-diynes with isocyanates leading to bicyclic pyridones.

Abstract

[reaction: see text] A ruthenium(II) complex possessing a planar Cp ligand, CpRu(cod)Cl, effectively catalyzed the [2 + 2 + 2] cycloaddition of 1,6-diynes with isocyanates to afford bicyclic pyridones in 58-87% yields.

Entities: Chemical

Year: 2001 PMID： 11418063 DOI： 10.1021/ol016082t

Source DB: PubMed Journal: Org Lett ISSN： 1523-7052 Impact factor: 6.005

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Cited

10 in total

1. Asymmetric synthesis of bicyclic amidines via rhodium-catalyzed [2+2+2] cycloaddition of carbodiimides.

Authors: Robert T Yu; Tomislav Rovis
Journal: J Am Chem Soc Date: 2008-02-27 Impact factor: 15.419

2. Predictable and regioselective insertion of internal unsymmetrical alkynes in rhodium-catalyzed cycloadditions with alkenyl isocyanates.

Authors: Rebecca Keller Friedman; Tomislav Rovis
Journal: J Am Chem Soc Date: 2009-08-05 Impact factor: 15.419

3. Regioselective rhodium-catalyzed intermolecular [2+2+2] cycloaddition of alkynes and isocyanates to form pyridones.

Authors: Kevin M Oberg; Ernest E Lee; Tomislav Rovis
Journal: Tetrahedron Date: 2009-06-27 Impact factor: 2.457

4. Efficient and divergent synthesis of polyfunctionalized 2-pyridones from β-keto amides.

Authors: Baochang Gao; Yufeng Sun; Jun Wang; Zhigang Yuan; Liwu Zu; Xu Zhang; Wenbin Liu
Journal: RSC Adv Date: 2018-10-01 Impact factor: 4.036

5. Enantioselective synthesis of indolizidines bearing quaternary substituted stereocenters via rhodium-catalyzed [2+2+2] cycloaddition of alkenyl isocyanates and terminal alkynes.

Authors: Ernest E Lee; Tomislav Rovis
Journal: Org Lett Date: 2008-02-20 Impact factor: 6.005

6. Enantioselective rhodium-catalyzed [2 + 2 + 2] cycloadditions of terminal alkynes and alkenyl isocyanates: mechanistic insights lead to a unified model that rationalizes product selectivity.

Authors: Derek M Dalton; Kevin M Oberg; Robert T Yu; Ernest E Lee; Stéphane Perreault; Mark Emil Oinen; Melissa L Pease; Guillaume Malik; Tomislav Rovis
Journal: J Am Chem Soc Date: 2009-11-04 Impact factor: 15.419

Ruthenium(II)-catalyzed cycloaddition of 1,6-diynes with isocyanates leading to bicyclic pyridones.

1. Asymmetric synthesis of bicyclic amidines via rhodium-catalyzed [2+2+2] cycloaddition of carbodiimides.

2. Predictable and regioselective insertion of internal unsymmetrical alkynes in rhodium-catalyzed cycloadditions with alkenyl isocyanates.

3. Regioselective rhodium-catalyzed intermolecular [2+2+2] cycloaddition of alkynes and isocyanates to form pyridones.

4. Efficient and divergent synthesis of polyfunctionalized 2-pyridones from β-keto amides.

5. Enantioselective synthesis of indolizidines bearing quaternary substituted stereocenters via rhodium-catalyzed [2+2+2] cycloaddition of alkenyl isocyanates and terminal alkynes.

6. Enantioselective rhodium-catalyzed [2 + 2 + 2] cycloadditions of terminal alkynes and alkenyl isocyanates: mechanistic insights lead to a unified model that rationalizes product selectivity.

7. Nickel-catalyzed cycloadditions of unsaturated hydrocarbons, aldehydes, and ketones.

Review 8. Ruthenium-Catalyzed Cycloadditions to Form Five-, Six-, and Seven-Membered Rings.

9. Rhodium-catalyzed asymmetric synthesis of silicon-stereogenic silicon-bridged arylpyridinones.

10. Diversity synthesis of complex pyridines yields a probe of a neurotrophic signaling pathway.