Enantioselective copper(I/II)-catalyzed conjugate addition of nitro esters to β,γ-unsaturated α-ketoesters

Sheng Zhang; Kun Xu; Fengfeng Guo; Yanbin Hu; Zhenggen Zha; Zhiyong Wang

doi:10.1002/chem.201303512

Enantioselective copper(I/II)-catalyzed conjugate addition of nitro esters to β,γ-unsaturated α-ketoesters

Chemistry. 2014 Jan 20;20(4):979-82. doi: 10.1002/chem.201303512. Epub 2014 Jan 8.

Authors

Sheng Zhang¹, Kun Xu, Fengfeng Guo, Yanbin Hu, Zhenggen Zha, Zhiyong Wang

Affiliation

¹ Hefei National Laboratory for Physical Sciences at Microscale, CAS Key Laboratory of Soft Matter Chemistry and Department of Chemistry, University of Science and Technology of China, Hefei, Anhui 230026 (China), Fax:(+86) 551-3603185.

PMID: 24403091
DOI: 10.1002/chem.201303512

Abstract

A highly enantioselective Michael addition of nitroacetates to β,γ-unsaturated α-ketoesters was developed by using chiral copper catalysts. The Michael addition products can be obtained in high yields with up to 99 % ee. With these densely functionalized products, the chiral cyclic nitrones, which are important synthetic intermediates, can be obtained in one step.

Keywords: Michael addition; asymmetric catalysis; copper; ketoesters; nitroacetate.