Rh-catalyzed asymmetric hydrogenation of gamma-phthalimido-substituted alpha,beta-unsaturated carboxylic acid esters: an efficient enantioselective synthesis of beta-aryl-gamma-amino acids

Deng, J.; Duan, Z-Chao.; Huang, J-Di.; Hu, X-Ping.; Wang, D-Yong.; Yu, S-Bo.; Xu, X-Feng.; Zheng, Z.

Organic Letters 9(23): 4825-4828


ISSN/ISBN: 1523-7060
PMID: 17929937
DOI: 10.1021/ol702193v
Accession: 021694658

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A series of chiral beta-aryl-gamma-amino acid ester derivatives were synthesized in high enantioselectivities (93-97% ee) via the Rh-catalyzed asymmetric hydrogenation of gamma-phthalimido-alpha,beta-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.