Literature DB >> 19739689

Nickel-catalyzed cycloadditive couplings of enynes and isocyanates.

Brendan R D'Souza1, Janis Louie.   

Abstract

A mild and general route for preparing dienamides is described. Nickel imidazolylidene complexes were used to mediate cycloadditive coupling between enynes and isocyanates. Dienamides were prepared in excellent yields and with good E:Z selectivity. These dienamides can be further manipulated through oxidative cyclization methods. When a terminal enyne is employed, cyclization affords a lactam rather than a dienamide.

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Year:  2009        PMID: 19739689      PMCID: PMC2792207          DOI: 10.1021/ol901703t

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


  16 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.  Nickel-catalyzed cycloaddition of unsaturated hydrocarbons and carbonyl compounds.

Authors:  Thomas N Tekavec; Thomas N Tekevac; Janis Louie
Journal:  Org Lett       Date:  2005-09-01       Impact factor: 6.005

3.  Preparation and electrophilic cyclization of multisubstituted dienamides leading to cyclic iminoethers.

Authors:  Congyang Wang; Jiang Lu; Guoliang Mao; Zhenfeng Xi
Journal:  J Org Chem       Date:  2005-06-24       Impact factor: 4.354

4.  A nickel-catalyzed route to pyridines.

Authors:  Michael M McCormick; Hung A Duong; Gang Zuo; Janis Louie
Journal:  J Am Chem Soc       Date:  2005-04-13       Impact factor: 15.419

5.  An in situ approach for nickel-catalyzed cycloaddition.

Authors:  Thomas N Tekavec; Gang Zuo; Kristina Simon; Janis Louie
Journal:  J Org Chem       Date:  2006-07-21       Impact factor: 4.354

6.  Selectivity in nickel-catalyzed rearrangements of cyclopropylen-ynes.

Authors:  Gang Zuo; Janis Louie
Journal:  J Am Chem Soc       Date:  2005-04-27       Impact factor: 15.419

7.  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

8.  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

9.  Nickel-catalyzed synthesis of acrylamides from alpha-olefins and isocyanates.

Authors:  Kristin D Schleicher; Timothy F Jamison
Journal:  Org Lett       Date:  2007-02-02       Impact factor: 6.005

10.  Coupling of Vinyl Aziridines and Isocyanates.

Authors:  Kainan Zhang; Pramod R Chopade; Janis Louie
Journal:  Tetrahedron Lett       Date:  2008       Impact factor: 2.415

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  1 in total

1.  Nickel-catalyzed cycloaddition of 1,3-dienes with 3-azetidinones and 3-oxetanones.

Authors:  Ashish Thakur; Megan E Facer; Janis Louie
Journal:  Angew Chem Int Ed Engl       Date:  2013-09-23       Impact factor: 15.336

  1 in total

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