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Volumn , Issue 10, 2003, Pages 1455-1458

Asymmetric synthesis of orthogonally protected (2S,4R)- and (2S,4S)-4-hydroxyornithine

Author keywords

4 hydroxyornithine; Amino acid; Asymmetric alkylation; Double stereo selection; Glycine template; Phase transfer catalyst

Indexed keywords

AMMONIUM DERIVATIVE; ESTER DERIVATIVE; N (DIPHENYLMETHYLENE)GLYCINE TERT BUTYL ESTER; N BENZOYLOXYCARBONYL 5 IODOMETHYLOXAZOLIDINE; ORNITHINE DERIVATIVE; OXAZOLIDINE DERIVATIVE; UNCLASSIFIED DRUG;

EID: 0043071423     PISSN: 09365214     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-2003-40840     Document Type: Article
Times cited : (22)

References (44)
  • 36
    • 0005159348 scopus 로고
    • Double asymmetric induction: (a) Horeau, A.; Kagan, H. B.; Vigneron, J. P. Bull. Soc. Chim. Fr. 1968, 3795. (b) Masamune, S.; Choy, W.; Petersen, J. S. ; Sita, L. R. Angew. Chem., Int. Ed. Engl. 1985, 24, 1.
    • (1968) Bull. Soc. Chim. Fr. , pp. 3795
    • Horeau, A.1    Kagan, H.B.2    Vigneron, J.P.3
  • 38
    • 0043105027 scopus 로고    scopus 로고
    • note
    • We thank one of the reviews for pointing out this control experiment. This result was not unexpected, but it didn't allow us to conclude whether the observed stereoselectivity in the presence of chiral ammonium salt was intrinsic to our substrate or was the consequence of the lack of the catalyst assistance.
  • 40
    • 0042103116 scopus 로고    scopus 로고
    • note
    • 20
  • 41
    • 0037415764 scopus 로고    scopus 로고
    • Double stereoselection using matched and mismatched chiral ammonium catalyst in the alkylation of a Gly-L-Phe derivative has been documented very recently, see: (a) Ooi, T.; Tayama, E.; Maruoka, K. Angew. Chem. Int. Ed. 2003, 42, 579. (b) For an earlier example of an achiral quarternary ammonium salt catalyzed alkylation of a dipeptide, see: O'Donnell, M. J.; Zhou, C.; Scott, W. L. J. Am. Chem. Soc. 1996, 118, 6070.
    • (2003) Angew. Chem. Int. Ed. , vol.42 , pp. 579
    • Ooi, T.1    Tayama, E.2    Maruoka, K.3
  • 42
    • 0030057825 scopus 로고    scopus 로고
    • Double stereoselection using matched and mismatched chiral ammonium catalyst in the alkylation of a Gly-L-Phe derivative has been documented very recently, see: (a) Ooi, T.; Tayama, E.; Maruoka, K. Angew. Chem. Int. Ed. 2003, 42, 579. (b) For an earlier example of an achiral quarternary ammonium salt catalyzed alkylation of a dipeptide, see: O'Donnell, M. J.; Zhou, C.; Scott, W. L. J. Am. Chem. Soc. 1996, 118, 6070.
    • (1996) J. Am. Chem. Soc. , vol.118 , pp. 6070
    • O'Donnell, M.J.1    Zhou, C.2    Scott, W.L.3


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.