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Highly enantioselective hydrogenation of alpha-arylmethylene cycloalkanones catalyzed by iridium complexes of chiral spiro aminophosphine ligands.
J Am Chem Soc. 2010 Apr 07; 132(13):4538-9.JA

Abstract

The highly efficient asymmetric hydrogenation of alpha-arylmethylene cycloalkanones catalyzed by Ir-complexes of chiral spiro aminophosphine ligands was developed, providing chiral exo-cyclic allylic alcohols at high yields with excellent enantioselectivities (up to 97% ee) and high turnover numbers (S/C up to 10,000). This new reaction provided an efficient method for the synthesis of the key intermediate of the active form of the anti-inflammatory loxoprofen.

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Publisher Full Text (DOI)

Authors+Show Affiliations

Xie JB
State Key Laboratory and Institute of Elemento-organic Chemistry, Nankai University, Tianjin 300071, China.
Xie JH
No affiliation info available
Liu XY
No affiliation info available
Kong WL
No affiliation info available
Li S
No affiliation info available
Zhou QL
No affiliation info available

MeSH

AlcoholsCatalysisHydrogenationIridiumKetonesLigandsMolecular StructureOrganometallic CompoundsPhosphinesSpiro CompoundsStereoisomerism

Pub Type(s)

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

Language

eng

PubMed ID

20232874

Citation

Xie, Jian-Bo, et al. "Highly Enantioselective Hydrogenation of Alpha-arylmethylene Cycloalkanones Catalyzed By Iridium Complexes of Chiral Spiro Aminophosphine Ligands." Journal of the American Chemical Society, vol. 132, no. 13, 2010, pp. 4538-9.
Xie JB, Xie JH, Liu XY, et al. Highly enantioselective hydrogenation of alpha-arylmethylene cycloalkanones catalyzed by iridium complexes of chiral spiro aminophosphine ligands. J Am Chem Soc. 2010;132(13):4538-9.
Xie, J. B., Xie, J. H., Liu, X. Y., Kong, W. L., Li, S., & Zhou, Q. L. (2010). Highly enantioselective hydrogenation of alpha-arylmethylene cycloalkanones catalyzed by iridium complexes of chiral spiro aminophosphine ligands. Journal of the American Chemical Society, 132(13), 4538-9. https://doi.org/10.1021/ja100652f
Xie JB, et al. Highly Enantioselective Hydrogenation of Alpha-arylmethylene Cycloalkanones Catalyzed By Iridium Complexes of Chiral Spiro Aminophosphine Ligands. J Am Chem Soc. 2010 Apr 7;132(13):4538-9. PubMed PMID: 20232874.
* Article titles in AMA citation format should be in sentence-case
TY - JOUR T1 - Highly enantioselective hydrogenation of alpha-arylmethylene cycloalkanones catalyzed by iridium complexes of chiral spiro aminophosphine ligands. AU - Xie,Jian-Bo, AU - Xie,Jian-Hua, AU - Liu,Xiao-Yan, AU - Kong,Wei-Ling, AU - Li,Shen, AU - Zhou,Qi-Lin, PY - 2010/3/18/entrez PY - 2010/3/18/pubmed PY - 2010/7/14/medline SP - 4538 EP - 9 JF - Journal of the American Chemical Society JO - J Am Chem Soc VL - 132 IS - 13 N2 - The highly efficient asymmetric hydrogenation of alpha-arylmethylene cycloalkanones catalyzed by Ir-complexes of chiral spiro aminophosphine ligands was developed, providing chiral exo-cyclic allylic alcohols at high yields with excellent enantioselectivities (up to 97% ee) and high turnover numbers (S/C up to 10,000). This new reaction provided an efficient method for the synthesis of the key intermediate of the active form of the anti-inflammatory loxoprofen. SN - 1520-5126 UR - https://www.unboundmedicine.com/medline/citation/20232874/Highly_enantioselective_hydrogenation_of_alpha_arylmethylene_cycloalkanones_catalyzed_by_iridium_complexes_of_chiral_spiro_aminophosphine_ligands_ DB - PRIME DP - Unbound Medicine ER -