Literature DB >> 12722067

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

Susan E Gibson1, Andrea Stevenazzi.   

Abstract

As a consequence of growing environmental awareness, it is now inappropriate to design a synthetic metal-mediated transformation that involves a noncatalytic use of toxic and expensive transition-metal species. One of the earliest examples of such a metal-mediated transformation is the Pauson-Khand reaction, a [2+2+1] cyclocarbonylation that generates a cyclopentenone. Despite the early descriptions by Pauson and co-workers of catalytic versions of the reaction with octacarbonyldicobalt(0), applications of the Pauson-Khand reaction have to date almost exclusively used approaches that involve stoichiometric quantities of cobalt-carbonyl complexes. In the last decade, and, most markedly, in the last two to three years, however, there have been many exciting and novel developments in the catalytic Pauson-Khand reaction. Furthermore, asymmetric catalysis of the Pauson-Khand reaction has been shown to be a viable process. In view of the impressive developments in Pauson-Khand catalysis in the last two to three years, we present a comprehensive and critical coverage of the catalytic Pauson-Khand reaction that is designed to facilitate its application and to point to exciting future developments.

Entities:  

Year:  2003        PMID: 12722067     DOI: 10.1002/anie.200200547

Source DB:  PubMed          Journal:  Angew Chem Int Ed Engl        ISSN: 1433-7851            Impact factor:   15.336


  11 in total

1.  A green chemistry approach to asymmetric catalysis: solvent-free and highly concentrated reactions.

Authors:  Patrick J Walsh; Hongmei Li; Cecilia Anaya de Parrodi
Journal:  Chem Rev       Date:  2007-05-27       Impact factor: 60.622

2.  Synthesis of acyclic alpha,beta-unsaturated ketones via Pd(II)-catalyzed intermolecular reaction of alkynamides and alkenes.

Authors:  Norie Momiyama; Matthew W Kanan; David R Liu
Journal:  J Am Chem Soc       Date:  2007-02-06       Impact factor: 15.419

3.  Regioselective Reductive Cross-Coupling Reactions of Unsymmetrical Alkynes.

Authors:  Holly A Reichard; Martin McLaughlin; Ming Z Chen; Glenn C Micalizio
Journal:  European J Org Chem       Date:  2010-01

4.  Metallacycle-Mediated Cross-Coupling with Substituted and Electronically Unactivated Alkenes.

Authors:  Holly A Reichard; Glenn C Micalizio
Journal:  Chem Sci       Date:  2011       Impact factor: 9.825

5.  Catalytic asymmetric synthesis of all-carbon quaternary stereocenters.

Authors:  Christopher J Douglas; Larry E Overman
Journal:  Proc Natl Acad Sci U S A       Date:  2004-01-14       Impact factor: 11.205

6.  Rh(I)-catalyzed cyclocarbonylation of allenol esters to prepare acetoxy 4-alkylidenecyclopent-3-en-2-ones.

Authors:  Kay M Brummond; Matthew M Davis; Chaofeng Huang
Journal:  J Org Chem       Date:  2009-11-06       Impact factor: 4.354

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

Authors:  Mahesh K Pallerla; Glenn P A Yap; Joseph M Fox
Journal:  J Org Chem       Date:  2008-07-19       Impact factor: 4.354

8.  From solvolysis to self-assembly.

Authors:  Peter J Stang
Journal:  J Org Chem       Date:  2009-01-02       Impact factor: 4.354

9.  An alkoxide-directed intermolecular [2+2+1] annulation: a three-component coupling reaction for the synthesis of tetrasubstituted alpha,beta-unsaturated gamma-lactams.

Authors:  Martin McLaughlin; Masayuki Takahashi; Glenn C Micalizio
Journal:  Angew Chem Int Ed Engl       Date:  2007       Impact factor: 15.336

10.  Rh(I)-catalyzed intramolecular [2 + 2 + 1] cycloaddition of allenenes: Construction of bicyclo[4.3.0]nonenones with an angular methyl group and tricyclo[6.4.0.0]dodecenone.

Authors:  Fuyuhiko Inagaki; Naoya Itoh; Yujiro Hayashi; Yumi Matsui; Chisato Mukai
Journal:  Beilstein J Org Chem       Date:  2011-04-07       Impact factor: 2.883

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