Ru-catalyzed highly enantioselective hydrogenation of beta-alkyl-substituted beta-(acylamino)acrylates

Jing Wu; Xuanhua Chen; Rongwei Guo; Chi-hung Yeung; Albert S C Chan

doi:10.1021/jo026675x

Ru-catalyzed highly enantioselective hydrogenation of beta-alkyl-substituted beta-(acylamino)acrylates

J Org Chem. 2003 Mar 21;68(6):2490-3. doi: 10.1021/jo026675x.

Authors

Jing Wu¹, Xuanhua Chen, Rongwei Guo, Chi-hung Yeung, Albert S C Chan

Affiliation

¹ Open Laboratory of Chirotechnology of the Institute of Molecular Technology for Drug Discovery and Synthesis and Department of Applied Biology and Chemical Technology, The Hong Kong Polytechnic University, Hong Kong.

PMID: 12636424
DOI: 10.1021/jo026675x

Abstract

Highly enantioselective hydrogenation of beta-alkyl-substituted (E)-beta-(acylamino)-acrylates catalyzed by Ru((R)-Xyl-P-Phos)(C(6)H(6))Cl(2) complex (cat. 1c) was achieved in up to 99.7% ee. Moderate to good enantioselectivities in the hydrogenation of corresponding (Z)-isomers in the presence of [Rh((R)-Xyl-P-Phos)(COD)]BF(4) (cat. 2c) were also obtained. The results demonstrated that the electronic and steric properties of the dipyridylphosphine ligands as well as the different transition metal ions have significant influences on the catalytic properties in the hydrogenation of beta-(acylamino)acrylates.