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Volumn 4, Issue 24, 2002, Pages 4341-4344

Synthesis of chiral chromium tricarbonyl labeled thymine PNA monomers via the Ugi reaction

Author keywords

[No Author keywords available]

Indexed keywords

CHROMIUM DERIVATIVE; DRUG DERIVATIVE; PEPTIDE NUCLEIC ACID; THYMINE;

EID: 0037191613     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol026994a     Document Type: Article
Times cited : (68)

References (26)
  • 2
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    • Dommling, A.; Ugi, I. Angew. Chem., Int. Ed. 2000, 39, 3168, Ugi, I. Pure Appl. Chem. 2001, 73, 187.
    • (2001) Pure Appl. Chem. , vol.73 , pp. 187
    • Ugi, I.1
  • 5
    • 0035256402 scopus 로고    scopus 로고
    • and references therein
    • Nielsen, P. E. Curr. Opin. Biotechnol. 2001, 12, 16 and references therein. Nielsen, P. E.; Egholm, M. Peptide Nucleic Acids. Protocols and Applications; Horizon Scientific Press: Norfolk, 1999.
    • (2001) Curr. Opin. Biotechnol. , vol.12 , pp. 16
    • Nielsen, P.E.1
  • 9
    • 0035857546 scopus 로고    scopus 로고
    • Jaouen G.; Salmain, M.; Vessieres, A.; Varenne, A.; Brossiers, P. J Organomet. Chem. 1999, 589, 92. Metzler-Nolte, N. Angew. Chem. Int. Ed. 2001, 40, 1040.
    • (2001) Angew. Chem. Int. Ed. , vol.40 , pp. 1040
    • Metzler-Nolte, N.1
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    • Marchelli, R.; Nielsen, P. E.; Sforza, S.; Haaima, G. Eur. J. Org. Chem. 1999, 197. Puschl, A.; Tedeschi, T.; Nielsen, P. E. Org. Lett. 2000, 2, 4161. Kumar, V. Eur. J. Org. Chem. 2002, 2021.
    • (2000) Org. Lett. , vol.2 , pp. 4161
    • Puschl, A.1    Tedeschi, T.2    Nielsen, P.E.3
  • 14
    • 0036310153 scopus 로고    scopus 로고
    • Marchelli, R.; Nielsen, P. E.; Sforza, S.; Haaima, G. Eur. J. Org. Chem. 1999, 197. Puschl, A.; Tedeschi, T.; Nielsen, P. E. Org. Lett. 2000, 2, 4161. Kumar, V. Eur. J. Org. Chem. 2002, 2021.
    • (2002) Eur. J. Org. Chem. , pp. 2021
    • Kumar, V.1
  • 15
    • 0016987417 scopus 로고
    • The use of (+)-α-ferrocenylethyl in a Ugi condensation has been reported: Ugi, I.; Eberle, G. Angew. Chem., Int. Ed. Engl. 1976, 15, 492. For a 4-component condensation of metal-stabilized hydrogen isocyanide, see: Kernbach, U.; Jaouen, G.; Mühl, M.; Polborn, K.; Fehlammer, W. P. Inorg. Chim. Acta 2002, 334, 45.
    • (1976) Angew. Chem., Int. Ed. Engl. , vol.15 , pp. 492
    • Ugi, I.1    Eberle, G.2
  • 16
    • 11144355468 scopus 로고    scopus 로고
    • The use of (+)-α-ferrocenylethyl in a Ugi condensation has been reported: Ugi, I.; Eberle, G. Angew. Chem., Int. Ed. Engl. 1976, 15, 492. For a 4-component condensation of metal-stabilized hydrogen isocyanide, see: Kernbach, U.; Jaouen, G.; Mühl, M.; Polborn, K.; Fehlammer, W. P. Inorg. Chim. Acta 2002, 334, 45.
    • (2002) Inorg. Chim. Acta , vol.334 , pp. 45
    • Kernbach, U.1    Jaouen, G.2    Mühl, M.3    Polborn, K.4    Fehlammer, W.P.5
  • 18
    • 0032785264 scopus 로고    scopus 로고
    • Rose-Munch, F.; Alexakis, A.; Rose, E.; Mangeney, P.; Marek, I.; Semra, A.; Robert, F. J. Am. Chem. Soc. 1992, 114, 8288. Rose, E.; Rose-Munch, F. Curr. Org. Chem. 1999, 3, 445.
    • (1999) Curr. Org. Chem. , vol.3 , pp. 445
    • Rose, E.1    Rose-Munch, F.2
  • 19
    • 0000178635 scopus 로고
    • Abel, E. W., Stone, F. G. A., Wilkinson, G., Eds.; Pergamon: Oxford
    • Davies, S. G.; McCarty, T. D. In Comprehensive Organometallic Chemistry II; Abel, E. W., Stone, F. G. A., Wilkinson, G., Eds.; Pergamon: Oxford, 1995; Vol. 12, p 1039. Solladié-Cavallo, A. In Advances in Metal-Organic Chemistry; Liebeskind, L. S., Ed.; JAI Press: Greenwich
    • (1995) Comprehensive Organometallic Chemistry II , vol.12 , pp. 1039
    • Davies, S.G.1    McCarty, T.D.2
  • 20
    • 0003969056 scopus 로고    scopus 로고
    • Liebeskind, L. S., Ed.; JAI Press: Greenwich
    • Davies, S. G.; McCarty, T. D. In Comprehensive Organometallic Chemistry II; Abel, E. W., Stone, F. G. A., Wilkinson, G., Eds.; Pergamon: Oxford, 1995; Vol. 12, p 1039. Solladié-Cavallo, A. In Advances in Metal-Organic Chemistry; Liebeskind, L. S., Ed.; JAI Press: Greenwich
    • Advances in Metal-Organic Chemistry
    • Solladié-Cavallo, A.1
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    • note
    • -1) 1877, 1968, 1681.
  • 24
    • 0041825971 scopus 로고
    • The hydrolytic step is crucial for the synthesis of enantiopure PNAs because of the presence of a benzyl proton that might lead to racemization in basic medium. However, it has been reported that deprotonation and subsequent electrophilic quenching at the benzylic position of arene chromiumtricarbonyl derivatives proceeds stereopecifically. See: Davies, S. G.; Blagg, J. Tetrahedron 1987, 41, 4463.
    • (1987) Tetrahedron , vol.41 , pp. 4463
    • Davies, S.G.1    Blagg, J.2
  • 25
    • 0042828088 scopus 로고    scopus 로고
    • Comparable yields were obtained from the reaction on the coresponding uncomplexed imine
    • Comparable yields were obtained from the reaction on the coresponding uncomplexed imine.


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