Literature DB >> 25600653

Oxidative asymmetric umpolung alkylation of Evans' β-ketoimides using dialkylzinc nucleophiles.

Tom A Targel1, Jayprakash N Kumar, O Svetlana Shneider, Sukanta Bar, Natalia Fridman, Shimon Maximenko, Alex M Szpilman.   

Abstract

Umpolung alkylation of Evans' auxiliary substituted β-ketoimides affords the diastereomerically pure products in yields ranging from 40 to 80%. The reaction itself proceeds with diastereoselectivities between 3 : 1 and 18 : 1. Dialkylzinc serves as the nucleophile and umpolung of the β-keto-imide enolate is achieved by the action of Koser's reagent.

Entities:  

Year:  2015        PMID: 25600653     DOI: 10.1039/c4ob02601b

Source DB:  PubMed          Journal:  Org Biomol Chem        ISSN: 1477-0520            Impact factor:   3.876


  3 in total

1.  Rh(II)-Catalyzed Reactions of Diazoesters with Organozinc Reagents.

Authors:  Robert Panish; Ramajeyam Selvaraj; Joseph M Fox
Journal:  Org Lett       Date:  2015-08-04       Impact factor: 6.005

2.  Chemoselective Intermolecular Cross-Enolate-Type Coupling of Amides.

Authors:  Daniel Kaiser; Christopher J Teskey; Pauline Adler; Nuno Maulide
Journal:  J Am Chem Soc       Date:  2017-11-03       Impact factor: 15.419

3.  Cross-coupling of dissimilar ketone enolates via enolonium species to afford non-symmetrical 1,4-diketones.

Authors:  Keshaba N Parida; Gulab K Pathe; Shimon Maksymenko; Alex M Szpilman
Journal:  Beilstein J Org Chem       Date:  2018-05-03       Impact factor: 2.883

  3 in total

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