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Volumn 64, Issue 16, 1999, Pages 5896-5903

Synthesis of hydroxamic esters via alkoxyaminocarbonylation of β- dicarbonyl compounds

Author keywords

[No Author keywords available]

Indexed keywords

1 TERT BUTOXY 5 METHOXYCARBONYLMETHYL 2 OXO PYRROLIDINE 3,3 DICARBOXYLIC ACID; 2 HYDROXYCARBAMOYL 2 METHYLMALONIC ACID DIETHYL ESTER; HYDROXAMIC ACID; UNCLASSIFIED DRUG;

EID: 0033529723     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo990353k     Document Type: Article
Times cited : (45)

References (42)
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    • For reviews, see: (a) Sandler, S. R.; Karo, W. In Organic Functional Group Preparations; Wasserman, H. H., Ed.; Academic Press: San Diego, 1989; Vol. 3, pp 482-522. (b) Bauer, L.; Exner, O.; Angew. Chem., Int. Ed. Engl. 1974, 13, 376-384.
    • (1989) Organic Functional Group Preparations , vol.3 , pp. 482-522
    • Sandler, S.R.1    Karo, W.2
  • 14
    • 84982367300 scopus 로고
    • For reviews, see: (a) Sandler, S. R.; Karo, W. In Organic Functional Group Preparations; Wasserman, H. H., Ed.; Academic Press: San Diego, 1989; Vol. 3, pp 482-522. (b) Bauer, L.; Exner, O.; Angew. Chem., Int. Ed. Engl. 1974, 13, 376-384.
    • (1974) Angew. Chem., Int. Ed. Engl. , vol.13 , pp. 376-384
    • Bauer, L.1    Exner, O.2
  • 18
    • 33845185611 scopus 로고
    • For reviews, see: Erdik, E.; Ay, M. Chem. Rev. 1989, 89, 1947-1980. Greck, C. G., Genet, J. P. Synlett 1997, 741-748. Mulzer, J.; Altenbach, H. J.; Braun, M.; Krohn, K.; Reissig, H. U. Organic Synthesis Highlights; VCH Publishers: Weinheim, 1991; pp 45-53.
    • (1989) Chem. Rev. , vol.89 , pp. 1947-1980
    • Erdik, E.1    Ay, M.2
  • 19
    • 0345483767 scopus 로고    scopus 로고
    • For reviews, see: Erdik, E.; Ay, M. Chem. Rev. 1989, 89, 1947- 1980. Greck, C. G., Genet, J. P. Synlett 1997, 741-748. Mulzer, J.; Altenbach, H. J.; Braun, M.; Krohn, K.; Reissig, H. U. Organic Synthesis Highlights; VCH Publishers: Weinheim, 1991; pp 45-53.
    • (1997) Synlett , pp. 741-748
    • Greck, C.G.1    Genet, J.P.2
  • 26
    • 0344035627 scopus 로고    scopus 로고
    • Insolublity problems with toluene lowered the yields
    • Insolublity problems with toluene lowered the yields.
  • 28
    • 84990085779 scopus 로고
    • Lithium halides are known to increase the yields of enolate reactions. See, for example: Seebach, D. Angew. Chem., Int. Ed. Engl. 1988, 27, 1624-1654.
    • (1988) Angew. Chem., Int. Ed. Engl. , vol.27 , pp. 1624-1654
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    • note
    • 3 resulted in either no reaction, dialkylation on carbon, monoalkylation on nitrogen, or mixtures of carbon and nitrogen alkylation. Knoevenegal strategies were also unsuccessful.
  • 38
    • 0000931564 scopus 로고
    • For decarboxylation of a β-keto ester substrate, see: Aboulhoda, S. J.; Henin, F.; Muzart, J.; Thorey, C. Tetrahedron: Asymmetry 1994, 5, 1321-1326. Tsuji, J.; Minami, I. Acc. Chem. Res. 1987, 20, 140-145.
    • (1987) Acc. Chem. Res. , vol.20 , pp. 140-145
    • Tsuji, J.1    Minami, I.2
  • 40
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    • note
    • We thank one of the reviewers for suggesting the use of triethylsilane in conjunction with TFA. This appeared to give less colored solutions, but the yields were not improved.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.