Literature DB >> 11996555

Dramatic improvement of the enantiomeric excess in the asymmetric conjugate addition reaction using new experimental conditions.

A Alexakis1, C Benhaim, S Rosset, M Humam.   

Abstract

The asymmetric conjugate addition of dialkylzincs is usually performed with Cu(OTf)(2) in toluene. We show that by using a copper carboxylate in Et(2)O, THF, or EtOAc, we strongly improve the enantioselectivity with a given ligand. Ee values up to 99.1% could be reached with new ligands based on the induced atropisomerism of a simple biphenol unit. In addition, we show that the Lewis acid effect of Cu(OTf)(2) is not a significant.

Entities:  

Year:  2002        PMID: 11996555     DOI: 10.1021/ja025598k

Source DB:  PubMed          Journal:  J Am Chem Soc        ISSN: 0002-7863            Impact factor:   15.419


  4 in total

1.  Synthesis of unsymmetrical o-biphenols and o-binaphthols via silicon-tethered Pd-catalyzed C-H arylation.

Authors:  Chunhui Huang; Vladimir Gevorgyan
Journal:  Org Lett       Date:  2010-05-21       Impact factor: 6.005

2.  Catalytic asymmetric carbon-carbon bond formation using alkenes as alkylmetal equivalents.

Authors:  Rebecca M Maksymowicz; Philippe M C Roth; Stephen P Fletcher
Journal:  Nat Chem       Date:  2012-07-15       Impact factor: 24.427

3.  Copper-catalyzed asymmetric conjugate addition of Grignard reagents to cyclic enones.

Authors:  Ben L Feringa; Ramón Badorrey; Diego Peña; Syuzanna R Harutyunyan; Adriaan J Minnaard
Journal:  Proc Natl Acad Sci U S A       Date:  2004-04-09       Impact factor: 11.205

4.  New biphenol-based, fine-tunable monodentate phosphoramidite ligands for catalytic asymmetric transformations.

Authors:  Zihao Hua; Victor C Vassar; Hojae Choi; Iwao Ojima
Journal:  Proc Natl Acad Sci U S A       Date:  2004-03-12       Impact factor: 11.205

  4 in total

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