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An efficient enantioselective fluorination of various beta-ketoesters catalyzed by chiral palladium complexes.
J Am Chem Soc. 2002 Dec 11; 124(49):14530-1.JA

Abstract

Reflecting the importance of fluorinated organic compounds in medicinal chemistry, development of an efficient method for catalytic enantioselective fluorination is increasingly desirable. Using a novel palladium complex 2 (1-2.5 mol %), various beta-ketoesters including cyclic and acyclic substrates were fluorinated with excellent enantioselectivity in the range of 83-94% ee. It is environmentally advantageous that this reaction proceeds well in solvents such as EtOH, rather than usual organic solvents. Furthermore, the product was successfully tranformed into both alpha-fluoro beta-hydroxy and beta-amino acid derivatives, which should be extremely useful in developing novel drugs.

Authors+Show Affiliations

Institute of Multidisciplinary Research for Advanced Materials, Tohoku University, Katahira, Sendai, Miyagi 980-8577, Japan.No affiliation info availableNo affiliation info availableNo affiliation info availableNo affiliation info available

Pub Type(s)

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

Language

eng

PubMed ID

12465951

Citation

Hamashima, Yoshitaka, et al. "An Efficient Enantioselective Fluorination of Various Beta-ketoesters Catalyzed By Chiral Palladium Complexes." Journal of the American Chemical Society, vol. 124, no. 49, 2002, pp. 14530-1.
Hamashima Y, Yagi K, Takano H, et al. An efficient enantioselective fluorination of various beta-ketoesters catalyzed by chiral palladium complexes. J Am Chem Soc. 2002;124(49):14530-1.
Hamashima, Y., Yagi, K., Takano, H., Tamás, L., & Sodeoka, M. (2002). An efficient enantioselective fluorination of various beta-ketoesters catalyzed by chiral palladium complexes. Journal of the American Chemical Society, 124(49), 14530-1.
Hamashima Y, et al. An Efficient Enantioselective Fluorination of Various Beta-ketoesters Catalyzed By Chiral Palladium Complexes. J Am Chem Soc. 2002 Dec 11;124(49):14530-1. PubMed PMID: 12465951.
* Article titles in AMA citation format should be in sentence-case
TY - JOUR T1 - An efficient enantioselective fluorination of various beta-ketoesters catalyzed by chiral palladium complexes. AU - Hamashima,Yoshitaka, AU - Yagi,Kenji, AU - Takano,Hisashi, AU - Tamás,László, AU - Sodeoka,Mikiko, PY - 2002/12/6/pubmed PY - 2003/2/13/medline PY - 2002/12/6/entrez SP - 14530 EP - 1 JF - Journal of the American Chemical Society JO - J Am Chem Soc VL - 124 IS - 49 N2 - Reflecting the importance of fluorinated organic compounds in medicinal chemistry, development of an efficient method for catalytic enantioselective fluorination is increasingly desirable. Using a novel palladium complex 2 (1-2.5 mol %), various beta-ketoesters including cyclic and acyclic substrates were fluorinated with excellent enantioselectivity in the range of 83-94% ee. It is environmentally advantageous that this reaction proceeds well in solvents such as EtOH, rather than usual organic solvents. Furthermore, the product was successfully tranformed into both alpha-fluoro beta-hydroxy and beta-amino acid derivatives, which should be extremely useful in developing novel drugs. SN - 0002-7863 UR - https://www.unboundmedicine.com/medline/citation/12465951/An_efficient_enantioselective_fluorination_of_various_beta_ketoesters_catalyzed_by_chiral_palladium_complexes_ L2 - https://doi.org/10.1021/ja028464f DB - PRIME DP - Unbound Medicine ER -