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Rh-catalyzed asymmetric hydrogenation of gamma-phthalimido-substituted alpha,beta-unsaturated carboxylic acid esters: an efficient enantioselective synthesis of beta-aryl-gamma-amino acids.
Org Lett. 2007 Nov 08; 9(23):4825-8.OL

Abstract

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.

Authors+Show Affiliations

Deng J
Dalian Institute of Chemical Physics, Chinese Academy of Sciences, Dalian 116023, China.
Duan ZC
No affiliation info available
Huang JD
No affiliation info available
Hu XP
No affiliation info available
Wang DY
No affiliation info available
Yu SB
No affiliation info available
Xu XF
No affiliation info available
Zheng Z
No affiliation info available

MeSH

Amino AcidsBaclofenCatalysisEstersHydrogenationLigandsMolecular StructureRhodiumRolipramStereoisomerism

Pub Type(s)

Journal Article
Research Support, Non-U.S. Gov't

Language

eng

PubMed ID

17929937

Citation

Deng, Jun, et al. "Rh-catalyzed Asymmetric Hydrogenation of Gamma-phthalimido-substituted Alpha,beta-unsaturated Carboxylic Acid Esters: an Efficient Enantioselective Synthesis of Beta-aryl-gamma-amino Acids." Organic Letters, vol. 9, no. 23, 2007, pp. 4825-8.
Deng J, Duan ZC, Huang JD, et al. Rh-catalyzed asymmetric hydrogenation of gamma-phthalimido-substituted alpha,beta-unsaturated carboxylic acid esters: an efficient enantioselective synthesis of beta-aryl-gamma-amino acids. Org Lett. 2007;9(23):4825-8.
Deng, J., Duan, Z. C., Huang, J. D., Hu, X. P., Wang, D. Y., Yu, S. B., Xu, X. F., & Zheng, Z. (2007). Rh-catalyzed asymmetric hydrogenation of gamma-phthalimido-substituted alpha,beta-unsaturated carboxylic acid esters: an efficient enantioselective synthesis of beta-aryl-gamma-amino acids. Organic Letters, 9(23), 4825-8.
Deng J, et al. Rh-catalyzed Asymmetric Hydrogenation of Gamma-phthalimido-substituted Alpha,beta-unsaturated Carboxylic Acid Esters: an Efficient Enantioselective Synthesis of Beta-aryl-gamma-amino Acids. Org Lett. 2007 Nov 8;9(23):4825-8. PubMed PMID: 17929937.
* Article titles in AMA citation format should be in sentence-case
TY - JOUR T1 - Rh-catalyzed asymmetric hydrogenation of gamma-phthalimido-substituted alpha,beta-unsaturated carboxylic acid esters: an efficient enantioselective synthesis of beta-aryl-gamma-amino acids. AU - Deng,Jun, AU - Duan,Zheng-Chao, AU - Huang,Jia-Di, AU - Hu,Xiang-Ping, AU - Wang,Dao-Yong, AU - Yu,Sai-Bo, AU - Xu,Xue-Feng, AU - Zheng,Zhuo, Y1 - 2007/10/12/ PY - 2007/10/13/pubmed PY - 2007/12/12/medline PY - 2007/10/13/entrez SP - 4825 EP - 8 JF - Organic letters JO - Org Lett VL - 9 IS - 23 N2 - 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. SN - 1523-7060 UR - https://www.unboundmedicine.com/medline/citation/17929937/Rh_catalyzed_asymmetric_hydrogenation_of_gamma_phthalimido_substituted_alphabeta_unsaturated_carboxylic_acid_esters:_an_efficient_enantioselective_synthesis_of_beta_aryl_gamma_amino_acids_ L2 - https://doi.org/10.1021/ol702193v DB - PRIME DP - Unbound Medicine ER -