Literature DB >> 16839167

1,2-migration in rhodium(II) carbene transfer reaction: remarkable steric effect on migratory aptitude.

Fengping Xiao1, Jianbo Wang.   

Abstract

A series of diazo carbonyl compounds bearing different substituents have been prepared in order to investigate the steric effect in 1,2-migration reaction of rhodium(II) carbene. Through the investigation on the diazo decomposition of these compounds with Rh2(OAc)4, it was found that the steric effect could dramatically influence the migratory aptitude. In many cases, the steric effect could override the inherent electronic effect of the substituent.

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Year:  2006        PMID： 16839167     DOI： 10.1021/jo0605391

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


  4 in total

1.  Metal-catalyzed [1,2]-alkyl shift in allenyl ketones: synthesis of multisubstituted furans.

Authors:  Alexander S Dudnik; Vladimir Gevorgyan
Journal:  Angew Chem Int Ed Engl       Date:  2007       Impact factor: 15.336

2.  Pyridone annulation via tandem Curtius rearrangement/6π-electrocyclization: total synthesis of (-)-lyconadin C.

Authors:  Xiayun Cheng; Stephen P Waters
Journal:  Org Lett       Date:  2013-08-02       Impact factor: 6.005

3.  Pyridine group assisted addition of diazo-compounds to imines in the 3-CC reaction of 2-aminopyridines, aldehydes, and diazo-compounds.

Authors:  Anton V Gulevich; Victoria Helan; Donald J Wink; Vladimir Gevorgyan
Journal:  Org Lett       Date:  2013-02-01       Impact factor: 6.005

4.  Metal-catalyzed 1,2-shift of diverse migrating groups in allenyl systems as a new paradigm toward densely functionalized heterocycles.

Authors:  Alexander S Dudnik; Anna W Sromek; Marina Rubina; Joseph T Kim; Alexander V Kel'in; Vladimir Gevorgyan
Journal:  J Am Chem Soc       Date:  2008-01-04       Impact factor: 15.419
  4 in total

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