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Highly enantioselective Rh-catalyzed hydrogenation of beta,gamma-unsaturated phosphonates with chiral ferrocene-based monophosphoramidite ligands.
J Org Chem. 2009 Dec 04; 74(23):9191-4.JO

Abstract

An enantioselective synthesis of chiral alkylphosphonates bearing a beta-stereogenic center, based on the Rh-catalyzed asymmetric hydrogenation of corresponding beta-substituted beta,gamma-unsaturated phosphonates with a ferrocene-based monophosphoramidite ligand under the mild hydrogenation conditions, was developed, in which an ee value of up to 98% was obtained.

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Publisher Full Text (DOI)

Authors+Show Affiliations

Duan ZC
Dalian Institute of Chemical physics, Chinese Academy of Sciences, 457 Zhongshan Road, Dalian 116023, China.
Hu XP
No affiliation info available
Zhang C
No affiliation info available
Wang DY
No affiliation info available
Yu SB
No affiliation info available
Zheng Z
No affiliation info available

MeSH

AmidesCatalysisFerrous CompoundsHydrogenationLigandsMetallocenesOrganophosphonatesPhosphoric AcidsRhodiumStereoisomerism

Pub Type(s)

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

Language

eng

PubMed ID

19877610

Citation

Duan, Zheng-Chao, et al. "Highly Enantioselective Rh-catalyzed Hydrogenation of Beta,gamma-unsaturated Phosphonates With Chiral Ferrocene-based Monophosphoramidite Ligands." The Journal of Organic Chemistry, vol. 74, no. 23, 2009, pp. 9191-4.
Duan ZC, Hu XP, Zhang C, et al. Highly enantioselective Rh-catalyzed hydrogenation of beta,gamma-unsaturated phosphonates with chiral ferrocene-based monophosphoramidite ligands. J Org Chem. 2009;74(23):9191-4.
Duan, Z. C., Hu, X. P., Zhang, C., Wang, D. Y., Yu, S. B., & Zheng, Z. (2009). Highly enantioselective Rh-catalyzed hydrogenation of beta,gamma-unsaturated phosphonates with chiral ferrocene-based monophosphoramidite ligands. The Journal of Organic Chemistry, 74(23), 9191-4. https://doi.org/10.1021/jo901619c
Duan ZC, et al. Highly Enantioselective Rh-catalyzed Hydrogenation of Beta,gamma-unsaturated Phosphonates With Chiral Ferrocene-based Monophosphoramidite Ligands. J Org Chem. 2009 Dec 4;74(23):9191-4. PubMed PMID: 19877610.
* Article titles in AMA citation format should be in sentence-case
TY - JOUR T1 - Highly enantioselective Rh-catalyzed hydrogenation of beta,gamma-unsaturated phosphonates with chiral ferrocene-based monophosphoramidite ligands. AU - Duan,Zheng-Chao, AU - Hu,Xiang-Ping, AU - Zhang,Cheng, AU - Wang,Dao-Yong, AU - Yu,Sai-Bo, AU - Zheng,Zhuo, PY - 2009/11/3/entrez PY - 2009/11/3/pubmed PY - 2010/3/10/medline SP - 9191 EP - 4 JF - The Journal of organic chemistry JO - J Org Chem VL - 74 IS - 23 N2 - An enantioselective synthesis of chiral alkylphosphonates bearing a beta-stereogenic center, based on the Rh-catalyzed asymmetric hydrogenation of corresponding beta-substituted beta,gamma-unsaturated phosphonates with a ferrocene-based monophosphoramidite ligand under the mild hydrogenation conditions, was developed, in which an ee value of up to 98% was obtained. SN - 1520-6904 UR - https://www.unboundmedicine.com/medline/citation/19877610/Highly_enantioselective_Rh_catalyzed_hydrogenation_of_betagamma_unsaturated_phosphonates_with_chiral_ferrocene_based_monophosphoramidite_ligands_ L2 - https://doi.org/10.1021/jo901619c DB - PRIME DP - Unbound Medicine ER -