Jump to main content
Jump to site search

Issue 20, 2016
Previous Article Next Article

Brønsted base-catalyzed three-component coupling reaction of α-ketoesters, imines, and diethyl phosphite utilizing [1,2]-phospha-Brook rearrangement

Author affiliations

Abstract

A three-component coupling reaction of α-ketoesters, imines, and diethyl phosphite under Brønsted base catalysis was developed by utilizing the [1,2]-phospha-Brook rearrangement. The reaction involves the generation of ester enolates via the umpolung process, i.e., the chemoselective addition of diethyl phosphite to α-ketoesters followed by the [1,2]-phospha-Brook rearrangement, and the trapping of the resulting enolates by imines preferentially over α-ketoesters and protons. This operationally simple reaction can provide densely functionalized β-amino acid derivatives including an oxygen functionality at the α-position in good yields. The diastereoselectivity is highly dependent on the substrates and reaction temperature, which is attributed to the reversibility of the addition of the ester enolates to the imines. The methodology was further extended to the reaction of α-ketoesters, β-nitrostyrenes, and diethyl phosphite.

Graphical abstract: Brønsted base-catalyzed three-component coupling reaction of α-ketoesters, imines, and diethyl phosphite utilizing [1,2]-phospha-Brook rearrangement

Back to tab navigation

Supplementary files

Publication details

The article was received on 07 Apr 2016, accepted on 25 Apr 2016 and first published on 25 Apr 2016


Article type: Paper
DOI: 10.1039/C6OB00739B
Citation: Org. Biomol. Chem., 2016,14, 4704-4711
  •   Request permissions

    Brønsted base-catalyzed three-component coupling reaction of α-ketoesters, imines, and diethyl phosphite utilizing [1,2]-phospha-Brook rearrangement

    A. Kondoh and M. Terada, Org. Biomol. Chem., 2016, 14, 4704
    DOI: 10.1039/C6OB00739B

Search articles by author

Spotlight

Advertisements