Literature DB >> 19161317

Intermolecular antiselective and enantioselective reductive coupling of enones and aromatic aldehydes with chiral Rh(Phebox) catalysts.

Takushi Shiomi1, Takahiro Adachi, Jun-ichi Ito, Hisao Nishiyama.   

Abstract

The intermolecular reductive coupling reaction of cyclopent-2-enone and aromatic aldehydes was realized by chiral rhodium-(bisoxazolinyl)phenyl catalysts, Rh(Phebox-Ph)(OAc)(2)(H(2)O), with diphenymethylsilane as a hydride donor to give the corresponding beta-hydroxyketones in high anti-selectivity (up to 96%) with high enantioselectivity (up to 93%).

Entities:  

Year:  2009        PMID： 19161317     DOI： 10.1021/ol802939u

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


  6 in total

1.  Further Developments and Applications of Oxazoline-Containing Ligands in Asymmetric Catalysis.

Authors:  Robert Connon; Brendan Roche; Balaji V Rokade; Patrick J Guiry
Journal:  Chem Rev       Date:  2021-05-21       Impact factor: 60.622

2.  (Diisopinocampheyl)borane-mediated reductive aldol reactions of acrylate esters: enantioselective synthesis of anti-aldols.

Authors:  Christophe Allais; Philippe Nuhant; William R Roush
Journal:  Org Lett       Date:  2013-07-25       Impact factor: 6.005

3.  Catalytic Reductive Aldol and Mannich Reactions of Enone, Acrylate, and Vinyl Heteroaromatic Pronucleophiles.

Authors:  Cole C Meyer; Eliezer Ortiz; Michael J Krische
Journal:  Chem Rev       Date:  2020-03-19       Impact factor: 60.622

4.  Diisopinocampheylborane-mediated reductive aldol reactions: highly enantio- and diastereoselective synthesis of syn aldols from N-acryloylmorpholine.

Authors:  Philippe Nuhant; Christophe Allais; William R Roush
Journal:  Angew Chem Int Ed Engl       Date:  2013-07-01       Impact factor: 15.336

5.  PdII-Catalyzed Oxidative Aldehyde-sp2C-H Functionalization and Cyclization Using NHC with Mild Oxidant DMSO for the Selective Synthesis of Esters, Sugar-Based Analogues, and β-Hydroxy Chromanones: An 18O-Labeling Study.

Authors:  Satinath Sarkar; Radha M Laha; Rajendra N Mitra; Dilip K Maiti
Journal:  ACS Omega       Date:  2016-11-21

6.  Photocontrolled Cobalt Catalysis for Selective Hydroboration of α,β-Unsaturated Ketones.

Authors:  Frédéric Beltran; Enrico Bergamaschi; Ignacio Funes-Ardoiz; Christopher J Teskey
Journal:  Angew Chem Int Ed Engl       Date:  2020-09-11       Impact factor: 15.336
  6 in total

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