Literature DB >> 21927511

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

Kevin M Oberg1, Ernest E Lee, Tomislav Rovis.   

Abstract

A highly regioselective rhodium-catalyzed intermolecular [2+2+2] cycloaddition of terminal alkynes with a variety of isocyanates to provide 2- and 4-pyridones has been developed. This reaction proceeds in good to excellent yields and overcomes the problem of dimerization and trimerization through the use of phosphoramidite ligands. A CO migration in the metallacycle is proposed to account for the formation of 4-pyridone.

Entities:  

Year:  2009        PMID： 21927511      PMCID： PMC3172821          DOI： 10.1016/j.tet.2009.02.021

Source DB:  PubMed          Journal:  Tetrahedron        ISSN： 0040-4020            Impact factor:   2.457


  22 in total

1.  Recent advances in the transition-metal-catalyzed regioselective approaches to polysubstituted benzene derivatives.

Authors:  S Saito; Y Yamamoto
Journal:  Chem Rev       Date:  2000-08-09       Impact factor: 60.622

2.  Construction of pyridine rings by metal-mediated [2 + 2 + 2] cycloaddition.

Authors:  Jesús A Varela; Carlos Saá
Journal:  Chem Rev       Date:  2003-09       Impact factor: 60.622

Review 3.  Bacterial topoisomerase inhibitors: quinolone and pyridone antibacterial agents.

Authors:  Lester A Mitscher
Journal:  Chem Rev       Date:  2005-02       Impact factor: 60.622

4.  Total Synthesis of Dimethyl Sulfomycinamate.

Authors:  T. Ross Kelly; Fengrui Lang
Journal:  J Org Chem       Date:  1996-07-12       Impact factor: 4.354

5.  Rhodium-catalyzed chemo-, regio-, and enantioselective [2 + 2 + 2] cycloaddition of alkynes with isocyanates.

Authors:  Ken Tanaka; Azusa Wada; Keiichi Noguchi
Journal:  Org Lett       Date:  2005-10-13       Impact factor: 6.005

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

Authors:  Robert T Yu; Tomislav Rovis
Journal:  J Am Chem Soc       Date:  2006-03-08       Impact factor: 15.419

7.  Selective preparation of pyridines, pyridones, and iminopyridines from two different alkynes via azazirconacycles.

Authors:  Tamotsu Takahashi; Fu-Yu Tsai; Yanzhong Li; Hui Wang; Yoshihiko Kondo; Masamichi Yamanaka; Kiyohiko Nakajima; Martin Kotora
Journal:  J Am Chem Soc       Date:  2002-05-08       Impact factor: 15.419

8.  Convenient synthesis and transformation of 2,6-dichloro-4-iodopyridine.

Authors:  J V Mello; N S Finney
Journal:  Org Lett       Date:  2001-12-27       Impact factor: 6.005

9.  Enantioselective rhodium-catalyzed [2+2+2] cycloaddition of alkenyl isocyanates and terminal alkynes: application to the total synthesis of (+)-lasubine II.

Authors:  Robert T Yu; Tomislav Rovis
Journal:  J Am Chem Soc       Date:  2006-09-27       Impact factor: 15.419

10.  2-pyridones from cyanoacetamides and enecarbonyl compounds: application to the synthesis of nothapodytine B.

Authors:  Lionel Carles; Kesavaram Narkunan; Sébastien Penlou; Laurence Rousset; Denis Bouchu; Marco A Ciufolini
Journal:  J Org Chem       Date:  2002-06-14       Impact factor: 4.354
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  12 in total

1.  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

2.  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

3.  Pyridine synthesis from oximes and alkynes via rhodium(III) catalysis: Cp* and Cp(t) provide complementary selectivity.

Authors:  Todd K Hyster; Tomislav Rovis
Journal:  Chem Commun (Camb)       Date:  2011-10-10       Impact factor: 6.222

4.  Enantioselective rhodium-catalyzed [4+2] cycloaddition of α,β-unsaturated imines and isocyanates.

Authors:  Kevin M Oberg; Tomislav Rovis
Journal:  J Am Chem Soc       Date:  2011-03-14       Impact factor: 15.419

5.  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

6.  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

7.  The iron-catalyzed construction of 2-aminopyrimidines from alkynenitriles and cyanamides.

Authors:  Timothy K Lane; Minh H Nguyen; Brendan R D'Souza; Nathan A Spahn; Janis Louie
Journal:  Chem Commun (Camb)       Date:  2013-09-11       Impact factor: 6.222

8.  Multi-component cycloaddition approaches in the catalytic asymmetric synthesis of alkaloid targets.

Authors:  Stéphane Perreault; Tomislav Rovis
Journal:  Chem Soc Rev       Date:  2009-09-15       Impact factor: 54.564

9.  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

10.  Catalytic, asymmetric indolizidinone aza-quaternary stereocenter synthesis: expedient synthesis of the cylindricine alkaloid core.

Authors:  Derek M Dalton; Tomislav Rovis
Journal:  Org Lett       Date:  2013-04-30       Impact factor: 6.005
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