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Volumn 45, Issue 8, 2004, Pages 1675-1678

Highly enantioselective alkylation of glycine methyl and ethyl ester derivatives under phase-transfer conditions: Its synthetic advantage

Author keywords

Alkylation; Chiral quaternary ammonium bromide; Phase transfer catalysis; Schiff base of glycine ethyl ester

Indexed keywords

BENZOPHENONE; BROMINE; CARBON; ESTER DERIVATIVE; ETHYLENE OXIDE DERIVATIVE; FLUORINE; GLYCINE; HYDROGEN; METHYL GROUP; NITROGEN; SCHIFF BASE;

EID: 0842283440     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2003.12.102     Document Type: Article
Times cited : (49)

References (31)
  • 1
    • 0003795884 scopus 로고    scopus 로고
    • For recent reviews, see: Y. Sasson, & R. Neumann. London: Blackie Academic & Professional. Chapter 14
    • For recent reviews, see: Shioiri T. Sasson Y., Neumann R. Handbook of Phase-Transfer Catalysis. 1997;Blackie Academic & Professional, London. Chapter 14.
    • (1997) Handbook of Phase-Transfer Catalysis
    • Shioiri, T.1
  • 3
    • 0003520820 scopus 로고    scopus 로고
    • F. Vogtle, J.F. Stoddart, & M. Shibasaki. Weinheim: Wiley-VCH
    • Shioiri T., Arai S. Vogtle F., Stoddart J.F., Shibasaki M. Stimulating Concepts in Chemistry. 2000;123 Wiley-VCH, Weinheim.
    • (2000) Stimulating Concepts in Chemistry , pp. 123
    • Shioiri, T.1    Arai, S.2
  • 7
    • 33845185214 scopus 로고
    • Effect of ester group on the enantioselectivity has been documented. See:
    • Effect of ester group on the enantioselectivity has been documented. See: O'Donnell M.J., Bennett W.D., Wu S. J. Am. Chem. Soc. 111:1989;2353.
    • (1989) J. Am. Chem. Soc. , vol.111 , pp. 2353
    • O'Donnell, M.J.1    Bennett, W.D.2    Wu, S.3
  • 22
    • 0034619177 scopus 로고    scopus 로고
    • 2a and 2b have often been employed in the transition metal-catalyzed asymmetric allylic alkylations. For recent selected examples, see: You S.-L., Hou X.-L., Dai L.-X., Cao B.-X., Sun J. Chem. Commun. 2000;1933.
    • (2000) Chem. Commun. , pp. 1933
    • You, S.-L.1    Hou, X.-L.2    Dai, L.-X.3    Cao, B.-X.4    Sun, J.5
  • 25
    • 85102984622 scopus 로고    scopus 로고
    • note
    • 3b.
  • 26
    • 85077848655 scopus 로고
    • For the vast synthetic utility of optically active α-amino aldehydes, see:
    • For the vast synthetic utility of optically active α-amino aldehydes, see: Tramontini M. Synthesis. 1982;605.
    • (1982) Synthesis , pp. 605
    • Tramontini, M.1
  • 31
    • 0842297121 scopus 로고    scopus 로고
    • note
    • 4/MeOH; DAICEL Chiralpak AD-H, λ=300 nm, hexane/EtOH=15:1, flow rate=0.5 mL/min, retention time: 22.4 min (S), 29.7 min (R).


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.