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Enantioselective synthesis of beta2-amino acids via Rh-catalyzed asymmetric hydrogenation with BoPhoz-type ligands: important influence of an N-H proton in the ligand on the enantioselectivity.
J Org Chem. 2008 Mar 07; 73(5):2015-7.JO

Abstract

A series of BoPhoz-type ligands were successfully applied in the rhodium-catalyzed asymmetric hydrogenation of a number of beta-substituted or unsubstituted alpha-(phthalimidomethyl)acrylates, affording good to excellent enantioselectivities. The results suggested that the presence of an N-H proton in the BoPhoz backbone could significantly improve the enantioselectivity, and ligand (Sc,Rp)-1d, bearing two CF3-groups in the 3,5-position of the phenyl ring of aminophosphino moiety, showed the highest enantioselectivity.

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Publisher Full Text (DOI)

Authors+Show Affiliations

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

MeSH

Amino AcidsLigandsMagnetic Resonance SpectroscopyOrganophosphonatesRhodiumSpectrometry, Mass, Electrospray IonizationStereoisomerism

Pub Type(s)

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

Language

eng

PubMed ID

18229942

Citation

Deng, Jun, et al. "Enantioselective Synthesis of Beta2-amino Acids Via Rh-catalyzed Asymmetric Hydrogenation With BoPhoz-type Ligands: Important Influence of an N-H Proton in the Ligand On the Enantioselectivity." The Journal of Organic Chemistry, vol. 73, no. 5, 2008, pp. 2015-7.
Deng J, Hu XP, Huang JD, et al. Enantioselective synthesis of beta2-amino acids via Rh-catalyzed asymmetric hydrogenation with BoPhoz-type ligands: important influence of an N-H proton in the ligand on the enantioselectivity. J Org Chem. 2008;73(5):2015-7.
Deng, J., Hu, X. P., Huang, J. D., Yu, S. B., Wang, D. Y., Duan, Z. C., & Zheng, Z. (2008). Enantioselective synthesis of beta2-amino acids via Rh-catalyzed asymmetric hydrogenation with BoPhoz-type ligands: important influence of an N-H proton in the ligand on the enantioselectivity. The Journal of Organic Chemistry, 73(5), 2015-7. https://doi.org/10.1021/jo702510m
Deng J, et al. Enantioselective Synthesis of Beta2-amino Acids Via Rh-catalyzed Asymmetric Hydrogenation With BoPhoz-type Ligands: Important Influence of an N-H Proton in the Ligand On the Enantioselectivity. J Org Chem. 2008 Mar 7;73(5):2015-7. PubMed PMID: 18229942.
* Article titles in AMA citation format should be in sentence-case
TY - JOUR T1 - Enantioselective synthesis of beta2-amino acids via Rh-catalyzed asymmetric hydrogenation with BoPhoz-type ligands: important influence of an N-H proton in the ligand on the enantioselectivity. AU - Deng,Jun, AU - Hu,Xiang-Ping, AU - Huang,Jia-Di, AU - Yu,Sai-Bo, AU - Wang,Dao-Yong, AU - Duan,Zheng-Chao, AU - Zheng,Zhuo, Y1 - 2008/01/30/ PY - 2008/1/31/pubmed PY - 2008/5/15/medline PY - 2008/1/31/entrez SP - 2015 EP - 7 JF - The Journal of organic chemistry JO - J Org Chem VL - 73 IS - 5 N2 - A series of BoPhoz-type ligands were successfully applied in the rhodium-catalyzed asymmetric hydrogenation of a number of beta-substituted or unsubstituted alpha-(phthalimidomethyl)acrylates, affording good to excellent enantioselectivities. The results suggested that the presence of an N-H proton in the BoPhoz backbone could significantly improve the enantioselectivity, and ligand (Sc,Rp)-1d, bearing two CF3-groups in the 3,5-position of the phenyl ring of aminophosphino moiety, showed the highest enantioselectivity. SN - 0022-3263 UR - https://www.unboundmedicine.com/medline/citation/18229942/Enantioselective_synthesis_of_beta2_amino_acids_via_Rh_catalyzed_asymmetric_hydrogenation_with_BoPhoz_type_ligands:_important_influence_of_an_N_H_proton_in_the_ligand_on_the_enantioselectivity_ DB - PRIME DP - Unbound Medicine ER -