Issue 4, 2016

Organocatalytic asymmetric conjugate addition of diaryloxazolidin-2,4-diones to nitroolefins: an efficient approach to chiral α-aryl-α-hydroxy carboxylic acids

Abstract

The first catalytic asymmetric conjugate addition of diaryloxazolidin-2,4-diones to nitroolefins is described. By employing an L-threonine-based tertiary amine-urea as the catalyst, the reaction proceeded in an excellent enantio- and diastereoselective manner (up to >99% ee and >19 : 1 dr). The adducts could be conveniently transformed to valuable α-aryl-α-hydroxy carboxylic acids, which structurally feature two adjacent hetero-quaternary and tertiary stereogenic centers.

Graphical abstract: Organocatalytic asymmetric conjugate addition of diaryloxazolidin-2,4-diones to nitroolefins: an efficient approach to chiral α-aryl-α-hydroxy carboxylic acids

Supplementary files

Article information

Article type
Research Article
Submitted
16 Dec 2015
Accepted
02 Feb 2016
First published
03 Feb 2016

Org. Chem. Front., 2016,3, 470-474

Organocatalytic asymmetric conjugate addition of diaryloxazolidin-2,4-diones to nitroolefins: an efficient approach to chiral α-aryl-α-hydroxy carboxylic acids

L. Jiao, X. Zhao, H. Liu, X. Ye, Y. Li and Z. Jiang, Org. Chem. Front., 2016, 3, 470 DOI: 10.1039/C5QO00428D

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