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Volumn 74, Issue 2, 2009, Pages 884-887

Nonracemizable isocyanoacetates for multicomponent reactions

Author keywords

[No Author keywords available]

Indexed keywords

DE PROTECTIONS; DI-PEPTIDES; MULTI-COMPONENT REACTIONS; ORTHO ESTERS;

EID: 60849117540     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo802420c     Document Type: Article
Times cited : (58)

References (30)
  • 7
    • 64549136968 scopus 로고    scopus 로고
    • Some isocyanoacetates are widely used in organic synthesis, where enhanced CH-acidity of them plays key role; see, for example:
    • Some isocyanoacetates are widely used in organic synthesis, where enhanced CH-acidity of them plays key role; see, for example:
  • 9
    • 0142042901 scopus 로고    scopus 로고
    • Bon, R. S.; Hong, C.; Bouma, M. J.; Schmitz, R. F.; de Kanter, F. J. J.; Lutz, M.; Spek, A. L.; A. Orru, R. V Org. Lett. 2003, 5, 3759-3762.
    • (b) Bon, R. S.; Hong, C.; Bouma, M. J.; Schmitz, R. F.; de Kanter, F. J. J.; Lutz, M.; Spek, A. L.; A. Orru, R. V Org. Lett. 2003, 5, 3759-3762.
  • 13
    • 0034956176 scopus 로고    scopus 로고
    • However, the ennantiomerically enriched α-isocyano acetamide is known to undergo the oxidative Ugi reaction without significant racemization, but amides are weaker CH-acids than esters; see: Ngouansavanh, T, Zhu, J. Angew. Chem
    • Bayer, T.; Riemer, C.; Kessler, H. J. Peptide Sci. 2001, 7, 250-261. However, the ennantiomerically enriched α-isocyano acetamide is known to undergo the oxidative Ugi reaction without significant racemization, but amides are weaker CH-acids than esters; see: Ngouansavanh, T.; Zhu, J. Angew. Chem.,
    • (2001) J. Peptide Sci , vol.7 , pp. 250-261
    • Bayer, T.1    Riemer, C.2    Kessler, H.3
  • 14
    • 64549083983 scopus 로고    scopus 로고
    • Int. Ed. 2007, 46, 5775.
    • (2007) , vol.5775 , Issue.46
    • Int, E.1
  • 20
    • 0027236202 scopus 로고    scopus 로고
    • Blaskovich, M. A.; Lajoie, G. A. J. Am. Chem. Soc. 1993, 115, 50215030.
    • Blaskovich, M. A.; Lajoie, G. A. J. Am. Chem. Soc. 1993, 115, 50215030.
  • 25
    • 0004361721 scopus 로고    scopus 로고
    • The synthesis of diformamide: (a) Allenstein, E.; Beyl, V Chem. Ber. 1967, 100, 3551-3563. Formylations by diformamide:
    • The synthesis of diformamide: (a) Allenstein, E.; Beyl, V Chem. Ber. 1967, 100, 3551-3563. Formylations by diformamide:
  • 28
    • 44349187052 scopus 로고    scopus 로고
    • CCDC 694486 contains the supplementary crystallographic data for 3e, Crystallographic Data Centre
    • CCDC 694486 contains the supplementary crystallographic data for 3e. These data can be obtained free of charge from The Cambridge Crystallographic Data Centre, www.ccdc.cam.ac.uk/data-request/cif.
    • These data can be obtained free of charge from The Cambridge
  • 29
    • 1542637533 scopus 로고
    • A few examples of β-elimination of HCN from isocyanides are known in literature; see, for example
    • A few examples of β-elimination of HCN from isocyanides are known in literature; see, for example: Jones, B. A.; Varma, M.; Stirling, C. J. M. J. Am. Chem. Soc. 1986, 108, 3153-3154.
    • (1986) J. Am. Chem. Soc , vol.108 , pp. 3153-3154
    • Jones, B.A.1    Varma, M.2    Stirling, C.J.M.3
  • 30
    • 64549105163 scopus 로고    scopus 로고
    • The saponification of 28 under the same conditions required only 30 min to complete.
    • The saponification of 28 under the same conditions required only 30 min to complete.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.