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Volumn 3, Issue 8, 2005, Pages 1435-1447

Asymmetric conjugate reductions with samarium diiodide: Asymmetric synthesis of (2S,3R)- And (2S,3S)-[2-2H,3-2H]-leucine-(S)- phenylalanine dipeptides and (2S,3R)-[2-2H,3-2H]- phenylalanine methyl ester

Author keywords

[No Author keywords available]

Indexed keywords

COMPLEXATION; ELECTRON TRANSITIONS; FLUORESCENCE; IODINE COMPOUNDS; MOLECULAR STRUCTURE; NUCLEAR MAGNETIC RESONANCE; SPECTROSCOPIC ANALYSIS; SYNTHESIS (CHEMICAL); TRANSITION METALS;

EID: 18444385349     PISSN: 14770520     EISSN: None     Source Type: Journal    
DOI: 10.1039/b500566c     Document Type: Article
Times cited : (42)

References (84)
  • 42
    • 0001367782 scopus 로고
    • ed. L. A. Paquette, John Wiley, New York
    • G. A. Molander, in Organic Reactions, ed. L. A. Paquette, John Wiley, New York, 1994, vol. 46, 211;
    • (1994) Organic Reactions , vol.46 , pp. 211
    • Molander, G.A.1
  • 54
    • 0010036491 scopus 로고    scopus 로고
    • For a review on the application of similar templates in synthesis, see: J. Liebscher and S. Jin, Chem. Soc. Rev., 1999, 28, 251.
    • (1999) Chem. Soc. Rev. , vol.28 , pp. 251
    • Liebscher, J.1    Jin, S.2
  • 56
  • 64
    • 18444373361 scopus 로고    scopus 로고
    • S. G. Davies and J. E. Thomson, unpublished data
    • S. G. Davies and J. E. Thomson, unpublished data.
  • 65
    • 18444416930 scopus 로고    scopus 로고
    • note
    • Me = 0.05 ppm (see ref. 15) while the (R) configuration of the 1′ stereogenic centre was tentatively assigned from the 3-H-1′-H coupling of 2.4 Hz assuming a hydrogen bond between the 1′-COH and 2-C=O.
  • 68
    • 18444384052 scopus 로고    scopus 로고
    • note
    • 19F NMR spectrum of the (R)-Moshers amide derivative and comparison with the authentic racemic sample.
  • 74
    • 4644245454 scopus 로고    scopus 로고
    • Similar dianions have been proposed as intermediates in the reduction of acyclic enamides, see: J. M. Concellón, M. Huerta and E. Bardales, Tetrahedron, 2004, 60, 10059.
    • (2004) Tetrahedron , vol.60 , pp. 10059
    • Concellón, J.M.1    Huerta, M.2    Bardales, E.3
  • 75
    • 0001140143 scopus 로고
    • For examples of protonation or deuteration of C-Sm(III) species with retention of configuration, sec: H. M. Walborsky and M. Topolski, J. Org. Chem., 1992, 57, 370;
    • (1992) J. Org. Chem. , vol.57 , pp. 370
    • Walborsky, H.M.1    Topolski, M.2


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.