Literature DB >> 21401131

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

Kevin M Oberg1, Tomislav Rovis.   

Abstract

A [4+2] cycloaddition of α,β-unsaturated imines and isocyanates catalyzed by a phosphoramidite-rhodium complex provides pyrimidinones in good yields and high enantioselectivities.
© 2011 American Chemical Society

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Year:  2011        PMID： 21401131      PMCID： PMC3069138          DOI： 10.1021/ja200766k

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


  28 in total

Review 1.  Genesis of dihydropyrimidinone(psi) calcium channel blockers: recent progress in structure-activity relationships and other effects.

Authors:  K Singh; D Arora; K Singh; S Singh
Journal:  Mini Rev Med Chem       Date:  2009-01       Impact factor: 3.862

Review 2.  Biologically active dihydropyrimidones of the Biginelli-type--a literature survey.

Authors:  C O Kappe
Journal:  Eur J Med Chem       Date:  2000-12       Impact factor: 6.514

3.  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

4.  Enantioselective [2 + 2 + 2] cycloaddition reaction of isocyanates and allenes catalyzed by nickel.

Authors:  Tomoya Miura; Masao Morimoto; Masahiro Murakami
Journal:  J Am Chem Soc       Date:  2010-09-14       Impact factor: 15.419

5.  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

6.  A Reexamination of the Mechanism of the Biginelli Dihydropyrimidine Synthesis. Support for an N-Acyliminium Ion Intermediate(1).

Authors:  C. Oliver Kappe
Journal:  J Org Chem       Date:  1997-10-17       Impact factor: 4.354

7.  1-Azadienes in cycloaddition and multicomponent reactions towards N-heterocycles.

Authors:  Bas Groenendaal; Eelco Ruijter; Romano V A Orru
Journal:  Chem Commun (Camb)       Date:  2008-09-08       Impact factor: 6.222

8.  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

9.  Total synthesis of indolizidine alkaloid (-)-209D: overriding substrate bias in the asymmetric rhodium-catalyzed [2+2+2] cycloaddition.

Authors:  Robert T Yu; Ernest E Lee; Guillaume Malik; Tomislav Rovis
Journal:  Angew Chem Int Ed Engl       Date:  2009       Impact factor: 15.336

10.  Excess substrate is a spectator ligand in a rhodium-catalyzed asymmetric [2 + 2 + 2] cycloaddition of alkenyl isocyanates with tolanes.

Authors:  Mark Emil Oinen; Robert T Yu; Tomislav Rovis
Journal:  Org Lett       Date:  2009-11-05       Impact factor: 6.005
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  6 in total

1.  Cationic dirhodium carboxylate-catalyzed synthesis of dihydropyrimidones from propargyl ureas.

Authors:  Miao Yang; Shannon J Odelberg; Zongzhong Tong; Dean Y Li; Ryan E Looper
Journal:  Tetrahedron       Date:  2013-07-08       Impact factor: 2.457

2.  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

3.  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

4.  Enantioselective Rhodium-Catalyzed [2+2+2] Cycloaddition of Pentenyl Isocyanate and 4-Ethynylanisole: Preparation and Use of Taddolpyrrolidine Phosphoramidite.

Authors:  Kevin M Oberg; Timothy J Martin; Mark Emil Oinen; Derek M Dalton; Rebecca Keller Friedman; Jamie M Neely; Tomislav Rovis
Journal:  Organic Synth       Date:  2014

5.  Highly diastereoselective synthesis of tetrahydropyridines by a C-H activation-cyclization-reduction cascade.

Authors:  Simon Duttwyler; Colin Lu; Arnold L Rheingold; Robert G Bergman; Jonathan A Ellman
Journal:  J Am Chem Soc       Date:  2012-02-22       Impact factor: 15.419

6.  Solvent-free synthesis, DNA-topoisomerase II activity and molecular docking study of new asymmetrically N,N'-substituted ureas.

Authors:  Andressa Esteves-Souza; Claudio E Rodrigues-Santos; Catarina de Nigris Del Cistia; Daniel Rosa da Silva; Carlos Maurício R Sant'anna; Aurea Echevarria
Journal:  Molecules       Date:  2012-11-01       Impact factor: 4.411
  6 in total

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