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Volumn 16, Issue 18, 2005, Pages 2989-2992

Diastereoselective alkylation of chiral 2-imidazolidinone glycolates: Asymmetric synthesis of α-hydroxy carboxylic acids

Author keywords

[No Author keywords available]

Indexed keywords

ALKALI; CARBOXYLIC ACID DERIVATIVE; GLYCOLIC ACID DERIVATIVE; HALIDE; SODIUM DERIVATIVE;

EID: 24944451383     PISSN: 09574166     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetasy.2005.07.036     Document Type: Article
Times cited : (9)

References (39)
  • 2
    • 0013505529 scopus 로고    scopus 로고
    • Principles of Asymmetric Synthesis
    • J.E. Baldwin P.D. Magnus Elsevier Press Oxford
    • R.E. Gawley, and J. Aube Principles of Asymmetric Synthesis J.E. Baldwin P.D. Magnus Tetrahedron Organic Chemistry Series Vol. 14 1996 Elsevier Press Oxford
    • (1996) Tetrahedron Organic Chemistry Series , vol.14
    • Gawley, R.E.1    Aube, J.2
  • 21
    • 0003905731 scopus 로고
    • J.D. Morrison Academic Press New York
    • D.A. Evans J.D. Morrison Asymmetric Synthesis Vol. 3 1984 Academic Press New York
    • (1984) Asymmetric Synthesis , vol.3
    • Evans, D.A.1
  • 33
    • 24944522670 scopus 로고    scopus 로고
    • note
    • 3, 300 MHz) δ 7.51-7.15 (m, 10H), 4.85-4.71 (m, 2H), 4.68 (s, 2H), 4.46-4.41 (m, 1H), 3.94 (t, 1H, J = 9.5 Hz), 3.58 (dd, 1H J = 9.7, 2.6 Hz), 2.52-2.47 (m, 1H), 0.97 (d, 3H, J = 7.0), 0.84
  • 35
    • 24944453382 scopus 로고    scopus 로고
    • note
    • 3,300 MHz) δ 7.38-7.14 (m, 15H), 5.29 (q, 1H, J = 6.6 Hz), 4.68-4.66 (m, 1H), 4.65 (d, 1H, J = 11.4 Hz), 4.47 (d, 1H, J = 11.4 Hz), 3.87 (t, 1H, J = 9.4 Hz), 3.58 (dd, 1H, J = 9.6, 2.3 Hz), 3.25 (dd, 1H, J = 13.4, 3.2 Hz), 2.82 (dd, 1H, J = 13.4, 9.0 Hz), 1.58 (d, 3H, J = 6.6 Hz)
  • 36
    • 0343990120 scopus 로고    scopus 로고
    • Prasad et al. reported that chiral N-acylated 2-imidazolidinones have been demonstrated to undergo highly diastereoselective benzylations and methylations via their sodium enolates and the chiral auxiliaries can be readily recycled with refluxing 2 M NaOH/dioxane (1:1) (30 min) without racemization; see: K. Konigsberger, K. Prasad, O. Repic, and T.J. Blacklock Tetrahedron: Asymmetry 8 1997 2347 2354
    • (1997) Tetrahedron: Asymmetry , vol.8 , pp. 2347-2354
    • Konigsberger, K.1    Prasad, K.2    Repic, O.3    Blacklock, T.J.4
  • 37
    • 24944488260 scopus 로고    scopus 로고
    • note
    • 15b [ α ] D 18 = + 54.0 (c 2.3, benzene); 4c: [ α ] D 19 = + 97.0 (c 0.71, EtOH).


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.