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Volumn 4, Issue 3, 2002, Pages 387-390

A catalyst that plays multiple roles: Asymmetric synthesis of β-substituted aspartic acid derivatives through a four-stage, one-pot procedure

Author keywords

[No Author keywords available]

Indexed keywords

ASPARTIC ACID; DRUG DERIVATIVE;

EID: 0037034309     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol017087t     Document Type: Article
Times cited : (88)

References (41)
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    • β-Hydroxyaspartic acids are present in many microorganisms
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    • (1975) J. Med. Chem. , vol.18 , pp. 354-358
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  • 11
    • 0016774502 scopus 로고
    • Various syntheses of L-erythro-β-hydroxyaspartic acid, a constituent of several proteins involved in the blood clotting cascade, have been reported
    • (c) Ishiyama, T.; Furuta, T.; Takai, M.; Okimoto, Y.; Aizawa, S.; Shiman, A.; Yonehara, H. J. Antibiot. 1975, 28, 821-823. Various syntheses of L-erythro-β-hydroxyaspartic acid, a constituent of several proteins involved in the blood clotting cascade, have been reported:
    • (1975) J. Antibiot. , vol.28 , pp. 821-823
    • Ishiyama, T.1    Furuta, T.2    Takai, M.3    Okimoto, Y.4    Aizawa, S.5    Shiman, A.6    Yonehara, H.7
  • 14
    • 0025082151 scopus 로고
    • Derivatives of β-alkoxy and hydroxy aspartates are known nontransportable glutamate transporter blockers
    • (f) Wagner, R.; Tilley, J. W.; Lovey, K. Synthesis 1990, 785-786. Derivatives of β-alkoxy and hydroxy aspartates are known nontransportable glutamate transporter blockers:
    • (1990) Synthesis , pp. 785-786
    • Wagner, R.1    Tilley, J.W.2    Lovey, K.3
  • 16
    • 0035886887 scopus 로고    scopus 로고
    • For a summary of recent asymmetric catalysis using nucleophiles, see: Dalko, P. I.; Moisan, L. Angew. Chem., Int. Ed. 2001, 40, 3726-3748.
    • (2001) Angew. Chem., Int. Ed. , vol.40 , pp. 3726-3748
    • Dalko, P.I.1    Moisan, L.2
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    • Lactone synthesis from ketenes
    • For other, excellent uses of cinchona alkaloids in asymmetric synthesis see the following. Ester synthesis from ketenes: (a) Samtleben, R.; Pracejus, H. J. Prakt. Chem. 1972, 314, 157-169. Lactone synthesis from ketenes:
    • (1972) J. Prakt. Chem. , vol.314 , pp. 157-169
    • Samtleben, R.1    Pracejus, H.2
  • 19
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    • Baylis-Hillman reaction
    • (c) Calter, M. A. J. Org. Chem. 1996, 61, 8006-8007. Baylis-Hillman reaction:
    • (1996) J. Org. Chem. , vol.61 , pp. 8006-8007
    • Calter, M.A.1
  • 24
    • 33845185214 scopus 로고    scopus 로고
    • (g) O'Donnell, M. J.; Bennett, W. D.; Wu, S. J. Am. Chem. Soc. 1989, 111, 2353-2355. Kacprzak, K.; Gawronski, J. Synthesis-Stuttgart 2001, 7, 961-998.
    • (2001) Synthesis-Stuttgart , vol.7 , pp. 961-998
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    • note
    • α-Chloroamine 5 is easily made by the condensation of benzamide with ethyl glyoxylate followed by reaction with oxalyl chloride. See Supporting Information.
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    • (c) Cole, D. C. Tetrahedron 1994, 50, 9517-9582.
    • (1994) Tetrahedron , vol.50 , pp. 9517-9582
    • Cole, D.C.1
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    • (b) Alder, R. W. Chem. Rev. 1989, 89, 1215-1223.
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    • note
    • Epimerization of the hydroxymethyl group in 9h was not observed under the reaction conditions.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.