Literature DB >> 15903306

1,2-vinyl and 1,2-acetylenyl migration in Rh(II) carbene reaction: remarkable bystander effect.

Weifeng Shi1, Fengping Xiao, Jianbo Wang.   

Abstract

A series of beta-(trichloroacetyl)amino alpha-diazo carbonyl compounds have been synthesized, and their Rh(II)-catalyzed reaction was investigated. 1,2-Migration was the predominant reaction pathway, and the migratory aptitude was found to be dramatically affected by the beta-substituents. The 1,2-vinyl and 1,2-acetylenyl group migration occurs preferentially in the presence of beta-hydrogen in Rh(2)(OAc)(4)-catalyzed reaction of beta-(trichloroacetyl)amino alpha-diazo carbonyl compounds. A possible reaction mechanism is discussed.

Entities:  

Year:  2005        PMID： 15903306     DOI： 10.1021/jo050173c

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


  4 in total

1.  Ring expansion and rearrangements of rhodium(II) azavinyl carbenes.

Authors:  Nicklas Selander; Brady T Worrell; Valery V Fokin
Journal:  Angew Chem Int Ed Engl       Date:  2012-11-19       Impact factor: 15.336

2.  Highly selective catalyst-dependent competitive 1,2-C→C, -O→C, and -N→C migrations from β-methylene-β-silyloxy-β-amido-α-diazoacetates.

Authors:  Xichen Xu; Yu Qian; Peter Y Zavalij; Michael P Doyle
Journal:  J Am Chem Soc       Date:  2013-01-17       Impact factor: 15.419

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.  Rhodium(I)-catalyzed cycloisomerizations of bicyclobutanes.

Authors:  Maciej A A Walczak; Peter Wipf
Journal:  J Am Chem Soc       Date:  2008-05-08       Impact factor: 15.419
  4 in total

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