Literature DB >> 18637694

Co-complexes derived from alkene insertion to alkyne-dicobaltpentacarbonyl complexes: insight into the regioselectivity of pauson-khand reactions of cyclopropenes.

Mahesh K Pallerla1, Glenn P A Yap, Joseph M Fox.   

Abstract

Described are the X-ray crystallographic and spectral properties of Co-complexes that were isolated from two Pauson-Khand reactions of chiral cyclopropenes. These are the first examples of isolated Co-complexes derived from the putative alkene-insertion intermediates of Pauson-Khand reactions. The binuclear Co-complexes are coordinated to mu-bonded, five-carbon "flyover" carbene ligands. It is proposed that the complexes result from cyclopropane fragmentation subsequent to alkene insertion. The observation of these metal complexes provides a rationale for the origin of regioselectivity in Pauson-Khand reactions of cyclopropenes.

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Year:  2008        PMID: 18637694      PMCID: PMC2667904          DOI: 10.1021/jo800776z

Source DB:  PubMed          Journal:  J Org Chem        ISSN: 0022-3263            Impact factor:   4.354


  14 in total

1.  Theoretical study of the regiochemistry-determining step of the Pauson-Khand reaction.

Authors:  T J de Bruin; A Milet; F Robert; Y Gimbert; A E Greene
Journal:  J Am Chem Soc       Date:  2001-07-25       Impact factor: 15.419

2.  Intermolecular Pauson-Khand reactions of cyclopropene: a general synthesis of cyclopentanones.

Authors:  I Marchueta; X Verdaguer; A Moyano; M A Pericàs; A Riera
Journal:  Org Lett       Date:  2001-10-04       Impact factor: 6.005

3.  The Pauson-Khand reaction: the catalytic age is here!

Authors:  Susan E Gibson; Andrea Stevenazzi
Journal:  Angew Chem Int Ed Engl       Date:  2003-04-25       Impact factor: 15.336

4.  Diastereoselective intermolecular Pauson-Khand reactions of chiral cyclopropenes.

Authors:  Mahesh K Pallerla; Joseph M Fox
Journal:  Org Lett       Date:  2005-08-04       Impact factor: 6.005

5.  X-ray crystal structure of an alkene-pentacarbonyldicobalt-alkyne complex: isolation of a stable Magnus-type Pauson-Khand reaction intermediate.

Authors:  Emilie V Banide; Helge Müller-Bunz; Anthony R Manning; Paul Evans; Michael J McGlinchey
Journal:  Angew Chem Int Ed Engl       Date:  2007       Impact factor: 15.336

Review 6.  The intermolecular Pauson-Khand reaction.

Authors:  Susan E Gibson; Nello Mainolfi
Journal:  Angew Chem Int Ed Engl       Date:  2005-05-13       Impact factor: 15.336

7.  Tetramethyl thiourea/Co2(CO)8-catalyzed Pauson-Khand reaction under balloon pressure of CO.

Authors:  Yefeng Tang; Lujiang Deng; Yandong Zhang; Guangbin Dong; Jiahua Chen; Zhen Yang
Journal:  Org Lett       Date:  2005-02-17       Impact factor: 6.005

8.  Silicon-mediated organic synthesis.

Authors:  L A Paquette
Journal:  Science       Date:  1982-08-27       Impact factor: 47.728

9.  Enantioselective synthesis of (-)-pentalenene.

Authors:  Mahesh K Pallerla; Joseph M Fox
Journal:  Org Lett       Date:  2007-11-22       Impact factor: 6.005

10.  Insight into the reactivity of olefins in the Pauson-Khand reaction.

Authors:  Theodorus J M de Bruin; Anne Milet; Andrew E Greene; Yves Gimbert
Journal:  J Org Chem       Date:  2004-02-20       Impact factor: 4.354

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  1 in total

1.  Functionalized Cyclopropenes and Methylenecyclopropenes from Dianions of 3-Hydroxymethylcyclopropenes.

Authors:  Matthew D Hassink; Joseph M Fox
Journal:  Synthesis (Stuttg)       Date:  2012       Impact factor: 3.157

  1 in total

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