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Volumn 45, Issue 5, 2004, Pages 1047-1050

Diastereoselective synthesis of 5-(alditol-1-C-yl)-hydantoins and their use as precursors of polyhydroxylated-α-amino acids

Author keywords

Hydantoin; Imidazolidin 2,4 dione

Indexed keywords

3,4,5 TRIHYDROXYNORVALINE; ALDEHYDE DERIVATIVE; AMINO ACID DERIVATIVE; CARBOHYDRATE DERIVATIVE; HYDANTOIN DERIVATIVE; UNCLASSIFIED DRUG;

EID: 0345761262     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2003.11.077     Document Type: Article
Times cited : (14)

References (48)
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  • 23
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    • An example of an aldol condensation of hydantoin derivatives with a C-4 aldehydo sugar has been reported:
    • An example of an aldol condensation of hydantoin derivatives with a C-4 aldehydo sugar has been reported: Mio S., Ichinose R., Goto K., Sugai S., Sato S. Tetrahedron. 47:1991;2111-2120.
    • (1991) Tetrahedron , vol.47 , pp. 2111-2120
    • Mio, S.1    Ichinose, R.2    Goto, K.3    Sugai, S.4    Sato, S.5
  • 30
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    • 5-(Alditol-1-C-yl)-hydantoin derivatives have been synthesized as intermediates for the synthesis of spirohydantoins or for their potential biological activity. See Refs. [7c,8b] and
    • 5-(Alditol-1-C-yl)-hydantoin derivatives have been synthesized as intermediates for the synthesis of spirohydantoins or for their potential biological activity. See Refs. [7c,8b] and Dziedzic B., Korohoda M.J., Rydzik E. Pol. J. Chem. 69:1995;90-94.
    • (1995) Pol. J. Chem. , vol.69 , pp. 90-94
    • Dziedzic, B.1    Korohoda, M.J.2    Rydzik, E.3
  • 34
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    • For the use of hydantoin chiral derivatives as glycine anion equivalents for the synthesis of α-alkyl and α, α-dialkyl α-amino acids see:
    • For the use of hydantoin chiral derivatives as glycine anion equivalents for the synthesis of α-alkyl and α, α-dialkyl α-amino acids see: Leon-Romo J.L., Virues C.I., Avina J., Regla I., Juaristi E. Chirality. 14:2002;144-150.
    • (2002) Chirality , vol.14 , pp. 144-150
    • Leon-Romo, J.L.1    Virues, C.I.2    Avina, J.3    Regla, I.4    Juaristi, E.5
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    • and references cited therein
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    • Veeresa, G.1    Datta, A.2
  • 40
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    • note
    • 3) δ 169.3, 156.4, 135.9, 135.2, 128.8, 128.6, 128.5, 128.0, 127.8, 48.9, 46.6, 42.5. White solid, mp 46-48 °C.
  • 41
    • 85030922370 scopus 로고    scopus 로고
    • note
    • 3).
  • 42
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    • note
    • 3).
  • 43
    • 85030933888 scopus 로고    scopus 로고
    • note
    • 2=1.018.
  • 44
    • 85030927879 scopus 로고    scopus 로고
    • Crystallographic data for this structure have been deposited with the Cambridge Crystallographic Data Centre as supplementary publication no. CCDC 220239. Copies of the data can be obtained free of charge on application to CCDC 12 Union Road, Cambridge CB2 1EZ (Fax: +44-1223-336-036. E-mail: deposit@ccdc.cam.ac.uk ).
  • 45
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    • The diastereoselectivity observed can be explained by the preferential formation of the cyclic transition state TS1 over TS2. Aldol reactions between α-chiral aldehydes and E(O)-enolates preferentially give the Felkin-type adduct by abiding both the Felkin-Anh rule and the Zimmerman-Traxler model
    • The diastereoselectivity observed can be explained by the preferential formation of the cyclic transition state TS1 over TS2. Aldol reactions between α-chiral aldehydes and E(O)-enolates preferentially give the Felkin-type adduct by abiding both the Felkin-Anh rule and the Zimmerman-Traxler model Mengel A., Reiser O. Chem. Rev. 99:1999;1191-1223.
    • (1999) Chem. Rev. , vol.99 , pp. 1191-1223
    • Mengel, A.1    Reiser, O.2
  • 48
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    • note
    • 3).


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.