Literature DB >> 16737302

Rhodium-catalyzed allyl transfer from homoallyl alcohols to aldehydes via retro-allylation followed by isomerization into ketones.

Yuko Takada1, Sayuri Hayashi, Koji Hirano, Hideki Yorimitsu, Koichiro Oshima.   

Abstract

Retro-allylation of homoallyl alcohol by rhodium catalysis occurs to generate allylrhodium species. This allylrhodium reacts with aldehydes to give the corresponding secondary alcohols in situ. Isomerization of these alcohols proceeds in the same pots to furnish the corresponding saturated ketones in good yields. [reaction: see text]

Entities:  

Year:  2006        PMID: 16737302     DOI: 10.1021/ol060710v

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


  4 in total

1.  Enthalpy vs Entropy Driven Complexation of Homoallylic Alcohols by Rh(I) Complexes.

Authors:  Sung Ok Kang; Vincent M Lynch; Victor W Day; Eric V Anslyn
Journal:  Organometallics       Date:  2011-10-25       Impact factor: 3.876

2.  Arylative Intramolecular Allylation of Ketones with 1,3-Enynes Enabled by Catalytic Alkenyl-to-Allyl 1,4-Rhodium(I) Migration.

Authors:  Benjamin M Partridge; Michael Callingham; William Lewis; Hon Wai Lam
Journal:  Angew Chem Int Ed Engl       Date:  2017-05-19       Impact factor: 15.336

3.  The isomerization of allylrhodium intermediates in the rhodium-catalyzed nucleophilic allylation of cyclic imines.

Authors:  Hamish B Hepburn; Hon Wai Lam
Journal:  Angew Chem Int Ed Engl       Date:  2014-09-09       Impact factor: 15.336

4.  Base-Promoted C-C Bond Activation Enables Radical Allylation with Homoallylic Alcohols.

Authors:  Maximilian Lübbesmeyer; Emily G Mackay; Mark A R Raycroft; Jonas Elfert; Derek A Pratt; Armido Studer
Journal:  J Am Chem Soc       Date:  2020-01-27       Impact factor: 15.419

  4 in total

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