Literature DB >> 16506740

Rhodium-catalyzed [2 + 2 + 2] cycloaddition of alkenyl isocyanates and alkynes.

Robert T Yu1, Tomislav Rovis.   

Abstract

A rhodium(I)-catalyzed [2 + 2 + 2] cycloaddition between alkenyl isocyanates and alkynes has been developed. Heating a mixture of an alkenyl isocyanate and a symmetrical internal alkyne in the presence of [Rh(ethylene)2Cl]2/P(4-OMe-C6H4)3 in toluene delivers substituted indolizinones and quinolizinones. Depending on the substrates, a rare fragmentation of the isocyanate unit can be involved within the cycloaddition process to furnish a vinylogous amide embedded in the indolizinone.

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Year:  2006        PMID： 16506740     DOI： 10.1021/ja057803c

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


  22 in total

1.  Synthesis of 6- and 7-membered cyclic enaminones: scope and mechanism.

Authors:  Micah J Niphakis; Brandon J Turunen; Gunda I Georg
Journal:  J Org Chem       Date:  2010-10-15       Impact factor: 4.354

2.  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

3.  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

4.  Phosphoramidite-Rhodium Complexes as Catalysts for the Asymmetric [2+2+2] Cycloaddition of Alkenyl Isocyanates and Alkynes.

Authors:  Rebecca Keller Friedman; Kevin M Oberg; Derek M Dalton; Tomislav Rovis
Journal:  Pure Appl Chem       Date:  2009-07-01       Impact factor: 2.453

5.  Enantioselective rhodium-catalyzed isomerization of 4-iminocrotonates: asymmetric synthesis of a unique chiral synthon.

Authors:  Wen-Zhen Zhang; John C K Chu; Kevin M Oberg; Tomislav Rovis
Journal:  J Am Chem Soc       Date:  2015-01-12       Impact factor: 15.419

Review 6.  Electronic and Steric Tuning of a Prototypical Piano Stool Complex: Rh(III) Catalysis for C-H Functionalization.

Authors:  Tiffany Piou; Tomislav Rovis
Journal:  Acc Chem Res       Date:  2017-12-22       Impact factor: 22.384

7.  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

8.  Bis(2-thien-yl)acetyl-ene.

Authors:  Emily M Harcourt; Daniel E Lynch; Darren G Hamilton
Journal:  Acta Crystallogr Sect E Struct Rep Online       Date:  2009-09-19

9.  Enantioselective rhodium-catalyzed [4+2+2] cycloaddition of dienyl isocyanates for the synthesis of bicyclic azocine rings.

Authors:  Robert T Yu; Rebecca Keller Friedman; Tomislav Rovis
Journal:  J Am Chem Soc       Date:  2009-09-23       Impact factor: 15.419

10.  Perfluorinated Taddol Phosphoramidite as an L,Z-Ligand on Rh(I) and Co(-I): Evidence for Bidentate Coordination via Metal-C6F5 Interaction.

Authors:  Derek M Dalton; Anthony K Rappé; Tomislav Rovis
Journal:  Chem Sci       Date:  2013-05-01       Impact factor: 9.825
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