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Volumn , Issue 18, 2007, Pages 2882-2884

Click chemistry: A straightforward route to decorated prolines

Author keywords

substituted prolines; 1,2,3 triazoles; Alkynes; Amino acids; Azides

Indexed keywords

PROLINE;

EID: 36549061413     PISSN: 09365214     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-2007-991065     Document Type: Article
Times cited : (12)

References (40)
  • 1
    • 0034712270 scopus 로고    scopus 로고
    • For a review on the stereoselective synthesis of α-alkylprolines, see
    • For a review on the stereoselective synthesis of α-alkylprolines, see: Cativiela, C.; Díaz-de-Villegas, M. D. Tetrahedron: Asymmetry 2000, 11, 645.
    • (2000) Tetrahedron: Asymmetry , vol.11 , pp. 645
    • Cativiela, C.1    Díaz-de-Villegas, M.D.2
  • 2
    • 0032561221 scopus 로고    scopus 로고
    • For other reviews on α,α-disubstituted α-amino acids, see: a
    • For other reviews on α,α-disubstituted α-amino acids, see: (a) Cativiela, C.; Díaz-de-Villegas, M. D. Tetrahedron: Asymmetry 1998, 9, 3517.
    • (1998) Tetrahedron: Asymmetry , vol.9 , pp. 3517
    • Cativiela, C.1    Díaz-de-Villegas, M.D.2
  • 20
    • 33846254547 scopus 로고    scopus 로고
    • For the synthesis of other proline-derived triazoles by azide-alkyne cycloadditions, see: a
    • For the synthesis of other proline-derived triazoles by azide-alkyne cycloadditions, see: (a) Yan, Z.-Y.; Niu, Y.-N.; Wei, H.-L.; Wu, L.-Y.; Zhao, Y.-B.; Liang, Y.-M. Tetrahedron: Asymmetry 2006, 17, 3288.
    • (2006) Tetrahedron: Asymmetry , vol.17 , pp. 3288
    • Yan, Z.-Y.1    Niu, Y.-N.2    Wei, H.-L.3    Wu, L.-Y.4    Zhao, Y.-B.5    Liang, Y.-M.6
  • 22
    • 36549064557 scopus 로고    scopus 로고
    • During our study, the preparation of racemic α-trifluoromethyl azahistidine analogues using the same approach has been reported: Shchetnikov, G. T.; Peredukov, A. S.; Osipov, S. N. Synlett 2007, 136.
    • During our study, the preparation of racemic α-trifluoromethyl azahistidine analogues using the same approach has been reported: Shchetnikov, G. T.; Peredukov, A. S.; Osipov, S. N. Synlett 2007, 136.
  • 29
    • 33748725421 scopus 로고    scopus 로고
    • A related compound of 5 (NBoc instead of NCbz) has been previously prepared in racemic form by propargylation of Boc-Pro-OMe: Ikeda, M.; Kugo, Y.; Kondo, Y.; Yamazaki, T.; Sato, T. J. Chem. Soc., Perkin Trans. 1 1997, 3339.
    • A related compound of 5 (NBoc instead of NCbz) has been previously prepared in racemic form by propargylation of Boc-Pro-OMe: Ikeda, M.; Kugo, Y.; Kondo, Y.; Yamazaki, T.; Sato, T. J. Chem. Soc., Perkin Trans. 1 1997, 3339.
  • 30
    • 36549062340 scopus 로고    scopus 로고
    • 1-Benzyl 2-Methyl (2R)-2-Prop-2-ynylpyrrolidine-1,2- dicarboxylate (4, To a solution of compound 5 (0.56 mmol, 197 mg) in MeOH (3 mL) in a microwave reaction tube was added TMSCl (2.89 mmol, 365 μL, The mixture was stirred for 2.5 h at 40°C using an irradiation power of 150 W with simultaneous cooling of the reaction vessel with a stream of compressed air. The solvent was removed under reduced pressure, and a sat. solution of NaHCO3 (3 mL) was added followed by carbobenzyloxy chloride (CbzCl, 0.62 mmol, 87 μL) at 0°C. The reaction mixture was allowed to warm to r.t, stirred overnight at r.t, and diluted with EtOAc. The two layers were separated, the aqueous layer was extracted with EtOAc and the combined organic layers were dried over Na2SO4, filtered, and concentrated under reduced pressure. The crude product was purified by chromatography on silica gel (eluent: PE-Et2O, 1:1) to give pure 7
    • 4: C, 67.76; H, 6.36; N, 4.65. Found: C, 67.57; H, 6.63; N, 4.93.
  • 36
    • 36549065052 scopus 로고    scopus 로고
    • 4, filtered, and concentrated under reduced pressure. The crude product was purified by chromatography on silica gel to afford analytically pure proline 9.
    • 4, filtered, and concentrated under reduced pressure. The crude product was purified by chromatography on silica gel to afford analytically pure proline 9.
  • 37
    • 36549036055 scopus 로고    scopus 로고
    • 1-Benzyl 2-Methyl (2R)-2, 1-(4-Ethoxy-4-oxobutyl)-1H-1,2,3-triazol-4-yl]methyl}pyrrolidine-1,2-dicarboxylate (9c, Rf0.28 (PE-Et2O, 1:1, 1H NMR (400 MHz, DMSO-d6, 110°C, δ, 7.52 (s, 1 H, triazole, 7.29-7.41 (m, 5 H, Ph, 5.12 (s, 2 H, CH2Ph, 4.34 (t, J, 6.9 Hz, 2 H, NCH2CH2CH2CO 2Et, 4.08 (q, J, 7.1 Hz, 2 H, CH2CH 3, 3.63 (br s, 3 H, OMe, 3.46-3.58 [m, 2 H, C(2)CHH, 5-Ha, 3.23 [d, J, 14.6 Hz, 1 H, C(2)CHH, 3.02-3.10 (m, 1 H, 5-H b, 2.24-2.32 (m, 1 H, 3-Ha, 2.27 (t, J, 7.3 Hz, 2 H, CH2CO2Et, 2.02-2.10 (m, 3 H, 3-Hb, CH2CH2CO2Et, 1.67-1.79 (m, 1 H, 4-Ha, 1.29-1.41 (m, 1 H, 4-Hb, 1.20 t, J, 7.1 Hz, 3
    • 6: C, 60.25; H, 6.59; N, 12.22. Found: C, 59.98; H, 6.90; N, 11.98.
  • 38
    • 4544344028 scopus 로고    scopus 로고
    • For previous examples of triazole-linked glycosyl amino acids and peptides, see: (a) Kuijpers, B. H. M.; Groothuys, S.; Keereweer, A. (B.) R.; Quaedflieg, P. J. L. M.; Blaauw, R. H.; van Delft, F. L.; Rutjes, F. P. J. T. Org. Lett. 2004, 6, 3123.
    • For previous examples of triazole-linked glycosyl amino acids and peptides, see: (a) Kuijpers, B. H. M.; Groothuys, S.; Keereweer, A. (B.) R.; Quaedflieg, P. J. L. M.; Blaauw, R. H.; van Delft, F. L.; Rutjes, F. P. J. T. Org. Lett. 2004, 6, 3123.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.