Jump to main content
Jump to site search
Access to RSC content Close the message box

Continue to access RSC content when you are not at your institution. Follow our step-by-step guide.


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

Article information


Submitted
07 Apr 2016
Accepted
25 Apr 2016
First published
25 Apr 2016

Org. Biomol. Chem., 2016,14, 4704-4711
Article type
Paper

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

Social activity

Search articles by author

Spotlight

Advertisements