Literature DB >> 23025546

Application of ruthenium complexes of triazole-containing tridentate ligands to asymmetric transfer hydrogenation of ketones.

Tarn C Johnson1, William G Totty, Martin Wills.   

Abstract

The synthesis of a series of tridentate ligands based on a homochiral 1,2-diamine structure attached to a triazole group and their subsequent applications to the asymmetric transfer hydrogenation of ketones are described. In the best cases, alcohols of up to 93% ee were obtained. Although base is not required, the use of Ru(3)(CO)(12) as metal source is essential, indicating a unique mechanism for the formation of the active catalyst.

Entities:  

Year:  2012        PMID: 23025546     DOI: 10.1021/ol302354z

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


  9 in total

1.  Diols as Dienophiles: Bridged Carbocycles via Ruthenium(0)-Catalyzed Transfer Hydrogenative Cycloadditions of Cyclohexadiene or Norbornadiene.

Authors:  Hiroki Sato; Keisuke Fukaya; Binit Sharma Poudel; Michael J Krische
Journal:  Angew Chem Int Ed Engl       Date:  2017-10-10       Impact factor: 15.336

2.  Ruthenium-catalyzed insertion of adjacent diol carbon atoms into C-C bonds: Entry to type II polyketides.

Authors:  Matthias Bender; Ben W H Turnbull; Brett R Ambler; Michael J Krische
Journal:  Science       Date:  2017-08-25       Impact factor: 47.728

3.  Regio- and diastereoselective C-C coupling of α-olefins and styrenes to 3-hydroxy-2-oxindoles by Ru-catalyzed hydrohydroxyalkylation.

Authors:  Eiji Yamaguchi; Jeffrey Mowat; Tom Luong; Michael J Krische
Journal:  Angew Chem Int Ed Engl       Date:  2013-07-05       Impact factor: 15.336

4.  Redox-triggered C-C coupling of diols and alkynes: synthesis of β,γ-unsaturated α-hydroxyketones and furans by ruthenium-catalyzed hydrohydroxyalkylation.

Authors:  Emma L McInturff; Khoa D Nguyen; Michael J Krische
Journal:  Angew Chem Int Ed Engl       Date:  2014-03-17       Impact factor: 15.336

5.  Ruthenium catalyzed hydrohydroxyalkylation of isoprene with heteroaromatic secondary alcohols: isolation and reversible formation of the putative metallacycle intermediate.

Authors:  Boyoung Y Park; T Patrick Montgomery; Victoria J Garza; Michael J Krische
Journal:  J Am Chem Soc       Date:  2013-10-24       Impact factor: 15.419

6.  Successive C-C coupling of dienes to vicinally dioxygenated hydrocarbons: ruthenium catalyzed [4 + 2] cycloaddition across the diol, hydroxycarbonyl, or dione oxidation levels.

Authors:  Laina M Geary; Ben W Glasspoole; Mary M Kim; Michael J Krische
Journal:  J Am Chem Soc       Date:  2013-02-28       Impact factor: 15.419

Review 7.  Ruthenium(0)-Catalyzed Cycloaddition of 1,2-Diols, Ketols, or Diones via Alcohol-Mediated Hydrogen Transfer.

Authors:  Hiroki Sato; Ben W H Turnbull; Keisuke Fukaya; Michael J Krische
Journal:  Angew Chem Int Ed Engl       Date:  2018-02-06       Impact factor: 15.336

8.  Ruthenium-catalyzed hydrohydroxyalkylation of acrylates with diols and α-hydroxycarbonyl compounds to form spiro- and α-methylene-γ-butyrolactones.

Authors:  Emma L McInturff; Jeffrey Mowat; Andrew R Waldeck; Michael J Krische
Journal:  J Am Chem Soc       Date:  2013-11-05       Impact factor: 15.419

9.  Homogeneous and heterogeneous photoredox-catalyzed hydroxymethylation of ketones and keto esters: catalyst screening, chemoselectivity and dilution effects.

Authors:  Axel G Griesbeck; Melissa Reckenthäler
Journal:  Beilstein J Org Chem       Date:  2014-05-19       Impact factor: 2.883

  9 in total

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