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Organocatalytic asymmetric conjugate addition of diaryloxazolidin-2,4-diones to nitroolefins: an efficient approach to chiral α-aryl-α-hydroxy carboxylic acids†
Lihui Jiao,Xiaowei Zhao,Xinyi Ye,Yun Li,Zhiyong Jiang
Organic Chemistry Frontiers Pub Date : 02/03/2016 00:00:00 , DOI:10.1039/C5QO00428D
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
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