Literature DB >> 18355073

Nickel-catalyzed allylation of allyl carbonates with homoallyl alcohols via retro-allylation providing 1,5-hexadienes.

Yuto Sumida1, Sayuri Hayashi, Koji Hirano, Hideki Yorimitsu, Koichiro Oshima.   

Abstract

A highly efficient and mild method for the synthesis of 1,5-hexadienes, nickel-catalyzed reactions of Boc-protected allyl alcohols with homoallyl alcohols, has been developed. Nickel-mediated retro-allylation allows for the use of homoallyl alcohols as allylmetal equivalents in the synthesis of 1,5-hexadienes.

Entities:  

Year:  2008        PMID： 18355073     DOI： 10.1021/ol800335v

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


  8 in total

1.  Deacylative allylation: allylic alkylation via retro-Claisen activation.

Authors:  Alexander J Grenning; Jon A Tunge
Journal:  J Am Chem Soc       Date:  2011-08-24       Impact factor: 15.419

2.  Diastereocontrol in asymmetric allyl-allyl cross-coupling: stereocontrolled reaction of prochiral allylboronates with prochiral allyl chlorides.

Authors:  Laura A Brozek; Michael J Ardolino; James P Morken
Journal:  J Am Chem Soc       Date:  2011-10-05       Impact factor: 15.419

3.  Integrating Allyl Electrophiles into Nickel-Catalyzed Conjunctive Cross-Coupling.

Authors:  Van T Tran; Zi-Qi Li; Timothy J Gallagher; Joseph Derosa; Peng Liu; Keary M Engle
Journal:  Angew Chem Int Ed Engl       Date:  2020-03-13       Impact factor: 15.336

4.  Catalytic enantioselective allyl-allyl cross-coupling with a borylated allylboronate.

Authors:  Hai Le; Robert E Kyne; Laura A Brozek; James P Morken
Journal:  Org Lett       Date:  2013-03-19       Impact factor: 6.005

5.  Enantioselective and site-specific copper-catalyzed reductive allyl-allyl cross-coupling of allenes.

Authors:  Guoxing Xu; Bin Fu; Haiyan Zhao; Yanfei Li; Ge Zhang; Ying Wang; Tao Xiong; Qian Zhang
Journal:  Chem Sci       Date:  2018-12-04       Impact factor: 9.825

6.  Catalytic stereospecific allyl-allyl cross-coupling of internal allyl electrophiles with AllylB(pin).

Authors:  Hai Le; Amanda Batten; James P Morken
Journal:  Org Lett       Date:  2014-04-04       Impact factor: 6.005

7.  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

8.  Photoinduced 1,2-dicarbofunctionalization of alkenes with organotrifluoroborate nucleophiles via radical/polar crossover.

Authors:  María Jesús Cabrera-Afonso; Anasheh Sookezian; Shorouk O Badir; Mirna El Khatib; Gary A Molander
Journal:  Chem Sci       Date:  2021-06-07       Impact factor: 9.969
  8 in total

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