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Volumn , Issue 4, 2008, Pages 578-582

Ruthenium-catalyzed cyclotrimerization of 1,6- and 1,7-azadiynes: New access to fluorinated bicyclic amino acids

Author keywords

Alkynes; Amino acids; Cyclotrimerization; Fluorinated diynes; Ruthenium catalysis

Indexed keywords

ALKYNE DERIVATIVE; AMINO ACID DERIVATIVE; RUTHENIUM;

EID: 40949129637     PISSN: 09365214     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-2008-1032089     Document Type: Article
Times cited : (35)

References (51)
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    • Kukhar, V. P, Soloshonok, V. A, Eds, John Wiley and Sons Ltd, New York, Brisbane, Toronto, and references cited therein
    • (a) Sewald, N.; Burger, K. Synthesis of Fluoro-Containing Amino Acids; Kukhar, V. P.; Soloshonok, V. A., Eds.; John Wiley and Sons Ltd.: New York, Brisbane, Toronto, 1995, 139; and references cited therein,
    • (1995) Synthesis of Fluoro-Containing Amino Acids , pp. 139
    • Sewald, N.1    Burger, K.2
  • 24
    • 0001800335 scopus 로고
    • For a review on synthetic applications of transition-metal-catalyzed acetylene cyclization, see
    • For a review on synthetic applications of transition-metal-catalyzed acetylene cyclization, see: Vollhardt, K. P. C. Acc. Chem. Res. 1977, 10, 1.
    • (1977) Acc. Chem. Res , vol.10 , pp. 1
    • Vollhardt, K.P.C.1
  • 26
    • 0001083027 scopus 로고
    • Angew. Chem. 1984, 96, 525.
    • (1984) Angew. Chem , vol.96 , pp. 525
  • 47
    • 40949102322 scopus 로고    scopus 로고
    • General Procedure for Ru-Catalyzed Cyclotrimerization: The catalyst RuCl(Cp*)(cod, 2 mol, was added to the solution of diyne (0.15 mmol) and alkyne (0.6 mmol) in degassed DCE under an argon atmosphere. The resulting mixture was stirred at r.t. until the reaction completion (TLC control, The solvent was removed under reduced pressure and the crude product was purified by column chromatography on silica gel (eluent: EtOAc-PE, Data for Compound 6a: oil. 1H NMR (400 MHz, DMSO-d6, 80 °C, δ, 3.61 (br s, 3 H, OMe, 4.84 (d, JAB, 15.2 Hz, 1 H, NCH2, 5.03 (d, JAB, 15.2 Hz, 1 H, NCH2, 5.23 (s, 2 H, OCH2, 7.34-7.56 (m, 9 H, Ar, 19F NMR (282 MHz, DMSO-d6, TFA, 80 °C, δ, 5.3 s, 3 F, CF3, Anal. Calcd for C19H 16F3NO4: C, 60.16; H, 4.25; N, 3.69. Found: C, 60.21; H
    • 4: C, 61.07; H, 4.61; N, 3.56. Found: C, 60.99; H, 4.55; N, 3.67.
  • 51
    • 40949164372 scopus 로고    scopus 로고
    • Data for Compound 10: mp 234 °C (dec, 1H NMR (300 MHz, DMSO-d6, δ, 3.35 (d, JAB, 15.4 Hz, 1 H, CH2, 3.39 (d, JAB, 15.4 Hz, 1 H, CH2, 3.86 (d, JAB, 15.5 Hz, 1 H, NCH 2, 4.06 (d, JAB, 15.5 Hz, 1 H, NCH2, 7.23 (m, 4 H, Ar, 19F NMR (282 MHz, DMSO-d6, δ, 3.07 (s, 3 F, CF3, 13C NMR (150.9 MHz, DMSO-d6, δ, 31.03, 45.12, 64.01 (q, 2JC-F, 29.9 Hz, 120.91 q, 1JC-F, 281.3 Hz, 127.31, 128.01, 128.41, 129.21, 133.81, 138.14, 168.41. Anal. Calcd for C12H12F3NO2: C, 53.88; H, 4.11; N, 5.71. Found: C, 53.61; H, 4.32; N, 5.34
    • 2: C, 53.88; H, 4.11; N, 5.71. Found: C, 53.61; H, 4.32; N, 5.34.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.