Literature DB >> 12418870

Efficient cu-catalyzed asymmetric conjugate additions of alkylzincs to trisubstituted cyclic enones.

Sylvia J Degrado1, Hirotake Mizutani, Amir H Hoveyda.   

Abstract

The first examples of efficient catalytic asymmetric conjugate addition (ACA) of alkylzincs to trisubstituted cyclic enones is disclosed. These Cu-catalyzed reactions proceed efficiently with five- and seven-membered ring substrates to afford the desired products in >/=95% ee. Intermediate enolates can be trapped with alkyl halides to generate a quaternary stereogenic center. The requisite chiral ligand is prepared from commercially available materials and can be used in situ without further purification in the presence of commercial grade (CuOTf)2.PhMe.

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Year:  2002        PMID: 12418870     DOI: 10.1021/ja021081x

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


  2 in total

1.  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

Review 2.  Diastereoselective and enantioselective conjugate addition reactions utilizing α,β-unsaturated amides and lactams.

Authors:  Katherine M Byrd
Journal:  Beilstein J Org Chem       Date:  2015-04-23       Impact factor: 2.883

  2 in total

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