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Volumn 71, Issue 11, 2006, Pages 4118-4129

Synthesis of (Z)-alkene and (E)-fluoroalkene-containing diketopiperazine mimetics utilizing organocopper-mediated reduction-alkylation and diastereoselectivity examination using DFT calculations

Author keywords

[No Author keywords available]

Indexed keywords

ALLYLLITHIUM COMPLEXES; BENZYL SIDE CHAIN; DIASTEREOSELECTIVITY EXAMINATION; DIKETOPIPERAZINE MIMETICS;

EID: 33646916569     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo060202z     Document Type: Article
Times cited : (32)

References (85)
  • 3
  • 41
    • 0000934125 scopus 로고    scopus 로고
    • Kazmierski, W. M., Ed.; Human Press: Totowa, NJ
    • (f) Welch, J. T.; Allmendinger, T. In Peptidomimetics Protocols; Kazmierski, W. M., Ed.; Human Press: Totowa, NJ, 1999; pp 357-384.
    • (1999) Peptidomimetics Protocols , pp. 357-384
    • Welch, J.T.1    Allmendinger, T.2
  • 66
    • 33646925188 scopus 로고    scopus 로고
    • note
    • N2′ reactions of phosphate derivatives. See ref 9.
  • 67
    • 33646948618 scopus 로고    scopus 로고
    • note
    • 1H NMR experiments: trans-24 (2.24 ppm) or trans-25 (2.46 ppm) vs cis-24 (2.85 ppm) or cis-25 (3.13 ppm).
  • 68
    • 33646929306 scopus 로고    scopus 로고
    • note
    • 2O.
  • 69
    • 33646945986 scopus 로고    scopus 로고
    • note
    • 1H NMR measurements. The proton at 1.87 ppm is likely to be affected by the anisotropic effect of the side chain phenyl ring, as in the case of alkene-series compounds. The structures of each of the isomers of 27 were assigned on the basis of the α-proton chemical shift: trans-21 (1.90 ppm) vs cis-27 (2.78 ppm). Compound 28 was assigned as a 3,6-trans isomer because the observed α-proton chemical shift (2.14 ppm) was similar to trans-27 or the upfield proton of 26.
  • 70
    • 0003622715 scopus 로고
    • Seminario, J. M., Politzer, P., Eds. Elsevier: New York, (Theoretical and Computational Chemistry)
    • (a) Seminario, J. M., Politzer, P., Eds. Modern Density Functional Theory. A Tool for Chemistry; Elsevier: New York, 1995; Vol. 2 (Theoretical and Computational Chemistry),
    • (1995) Modern Density Functional Theory. A Tool for Chemistry , vol.2
  • 73
    • 33646930144 scopus 로고    scopus 로고
    • note
    • The α-proton of trans-20 is supposed to be affected by the anisotropic effect of the phenyl ring in the X-ray structure. This supports the reliability of the above structure determinations.
  • 81
    • 33646916095 scopus 로고    scopus 로고
    • note
    • Compound 41 was synthesized by a procedure similar to the preparation of acetate 2. See Supporting Information.
  • 82
    • 33646906009 scopus 로고    scopus 로고
    • note
    • For structure determination of 42, see Supporting Information.
  • 83
    • 33646899676 scopus 로고    scopus 로고
    • note
    • The organocopper-mediated reduction-alkylation of N-methyl-alanine- derived substrate a was also performed. This reaction proceeded smoothly to yield α-methylated product b. HPLC analysis of the reaction mixture indicated that the predominant product of this reaction was the 3,6-cis isomer, as in the case of the reaction of acetate 41. We could not completely purify the product b and determine precise chemical yields as a result of its highly volatile nature.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.