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Enantioselective fluorination of tert-butoxycarbonyl lactones and lactams catalyzed by chiral Pd(II)-bisphosphine complexes.
J Org Chem. 2007 Jan 05; 72(1):246-50.JO

Abstract

An efficient catalytic enantioselective fluorination of tert-butoxycarbonyl lactones and lactams is reported. Reactions of the lactone substrates proceeded smoothly in an alcoholic solvent with a catalytic amount of chiral Pd(II) complex. In the case of the less acidic lactam substrates, concurrent use of the Pd complex and 2,6-lutidine as a cocatalyst was effective. Under the reaction conditions, the fluorinated lactones and lactams were obtained in good yield with excellent enantioselectivity (94-99% ee).

Authors+Show Affiliations

RIKEN, 2-1 Hirosawa, Wako, Saitama 351-0198, Japan.No 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

17194106

Citation

Suzuki, Toshiaki, et al. "Enantioselective Fluorination of Tert-butoxycarbonyl Lactones and Lactams Catalyzed By Chiral Pd(II)-bisphosphine Complexes." The Journal of Organic Chemistry, vol. 72, no. 1, 2007, pp. 246-50.
Suzuki T, Goto T, Hamashima Y, et al. Enantioselective fluorination of tert-butoxycarbonyl lactones and lactams catalyzed by chiral Pd(II)-bisphosphine complexes. J Org Chem. 2007;72(1):246-50.
Suzuki, T., Goto, T., Hamashima, Y., & Sodeoka, M. (2007). Enantioselective fluorination of tert-butoxycarbonyl lactones and lactams catalyzed by chiral Pd(II)-bisphosphine complexes. The Journal of Organic Chemistry, 72(1), 246-50.
Suzuki T, et al. Enantioselective Fluorination of Tert-butoxycarbonyl Lactones and Lactams Catalyzed By Chiral Pd(II)-bisphosphine Complexes. J Org Chem. 2007 Jan 5;72(1):246-50. PubMed PMID: 17194106.
* Article titles in AMA citation format should be in sentence-case
TY - JOUR T1 - Enantioselective fluorination of tert-butoxycarbonyl lactones and lactams catalyzed by chiral Pd(II)-bisphosphine complexes. AU - Suzuki,Toshiaki, AU - Goto,Tomomi, AU - Hamashima,Yoshitaka, AU - Sodeoka,Mikiko, PY - 2006/12/30/pubmed PY - 2007/2/14/medline PY - 2006/12/30/entrez SP - 246 EP - 50 JF - The Journal of organic chemistry JO - J Org Chem VL - 72 IS - 1 N2 - An efficient catalytic enantioselective fluorination of tert-butoxycarbonyl lactones and lactams is reported. Reactions of the lactone substrates proceeded smoothly in an alcoholic solvent with a catalytic amount of chiral Pd(II) complex. In the case of the less acidic lactam substrates, concurrent use of the Pd complex and 2,6-lutidine as a cocatalyst was effective. Under the reaction conditions, the fluorinated lactones and lactams were obtained in good yield with excellent enantioselectivity (94-99% ee). SN - 0022-3263 UR - https://www.unboundmedicine.com/medline/citation/17194106/Enantioselective_fluorination_of_tert_butoxycarbonyl_lactones_and_lactams_catalyzed_by_chiral_Pd_II__bisphosphine_complexes_ L2 - https://doi.org/10.1021/jo062048m DB - PRIME DP - Unbound Medicine ER -