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Rh-Catalyzed Asymmetric Hydrogenation of γ-Phthalimido-Substituted α,β-Unsaturated Carboxylic Acid Esters:  An Efficient Enantioselective Synthesis of β-Aryl-γ-amino Acids

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journal contribution
posted on 2007-11-08, 00:00 authored by Jun Deng, Zheng-Chao Duan, Jia-Di Huang, Xiang-Ping Hu, Dao-Yong Wang, Sai-Bo Yu, Xue-Feng Xu, Zhuo Zheng
A series of chiral β-aryl-γ-amino acid ester derivatives were synthesized in high enantioselectivities (93−97% ee) via the Rh-catalyzed asymmetric hydrogenation of γ-phthalimido-α,β-unsaturated carboxylic acid esters using highly modular chiral BoPhoz-type phosphine−aminophosphine ligands. The method has been applied successfully to the synthesis of several chiral pharmaceuticals including (R)-baclofen and (R)-rolipram with high enantioselectivities.