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Volumn 10, Issue 19, 2008, Pages 4303-4306

Two-step stereocontrolled synthesis of densely functionalized cyclic β-aminoesters containing four stereocenters, based on a new cerium(IV) ammonium nitrate catalyzed sequential three-component reaction

Author keywords

[No Author keywords available]

Indexed keywords

CERIUM; CERIUM(IV) AMMONIUM NITRATE; ESTER; NITRATE;

EID: 55449109761     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol801738d     Document Type: Article
Times cited : (59)

References (37)
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    • Gómez-Gallego, M.1    Mancheño, M.J.2    Sierra, M.A.3
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    • See also the periodical reviews published in the series Amino Acids, Peptides and Proteins (Royal Society of Chemistry).
    • (d) See also the periodical reviews published in the series Amino Acids, Peptides and Proteins (Royal Society of Chemistry).
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    • For a review of the structural and biological characteristices of peptides containing exclusively β-amino acids β-peptides, see: Gademann, K, Hintermann, T, Schreiber, J. V. Curr. Med. Chem. 1999, 6, 905
    • For a review of the structural and biological characteristices of peptides containing exclusively β-amino acids (β-peptides), see: Gademann, K.; Hintermann, T.; Schreiber, J. V. Curr. Med. Chem. 1999, 6, 905.
  • 24
    • 2542509173 scopus 로고    scopus 로고
    • For selected reviews and monographs on multicomponent reactions, see: a
    • For selected reviews and monographs on multicomponent reactions, see: (a) Dömling, A.; Ugi, I. Angew. Chem. Int. Ed. Engl. 2000, 39, 3168.
    • (2000) Angew. Chem. Int. Ed. Engl , vol.39 , pp. 3168
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    • (d) Ugi, A. Molecules 2003, 8, 53.
    • (2003) Molecules , vol.8 , pp. 53
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    • Zhu, J, Bienaymé, H, Eds, Wiley-VCH: Weinheim
    • (h) Zhu, J., Bienaymé, H., Eds. Multicomponent Reactions; Wiley-VCH: Weinheim, 2005.
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    • Dömling, A. Chem. Rev. 2006, 106, 17. For a symposium in print on this topic, see: Marek, I., Ed. Tetrahedron 2005, 67, 11299.
    • (i) Dömling, A. Chem. Rev. 2006, 106, 17. For a symposium in print on this topic, see: Marek, I., Ed. Tetrahedron 2005, 67, 11299.
  • 33
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    • In most reactions, compounds 5 were accompanied by small amounts 5-10, of the corresponding 1,3-cyclohexadiene derivatives, arising from elimination of a molecule of water
    • In most reactions, compounds 5 were accompanied by small amounts (5-10%) of the corresponding 1,3-cyclohexadiene derivatives, arising from elimination of a molecule of water.
  • 35
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    • Although the reaction described here is unprecedented, there is a literature report of the preparation of 1-acetyl-2-alkylamino-1,3-cyclohexadiene derivatives in 0-74% yield from β-enaminones and chalcones generated in situ from aryl bromides and propargyl alcohols. See: Schramm, O. G, Müller, T. J. J. Synlett 2006, 1841
    • Although the reaction described here is unprecedented, there is a literature report of the preparation of 1-acetyl-2-alkylamino-1,3-cyclohexadiene derivatives in 0-74% yield from β-enaminones and chalcones generated in situ from aryl bromides and propargyl alcohols. See: Schramm, O. G.; Müller, T. J. J. Synlett 2006, 1841.
  • 36
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    • For precedent of the fast generation of enaminones from amines and β-ketoesters under CAN catalysis, see: Sridharan, V, Avendaño, C, Menéndez, J. C. Synlett 2007, 881
    • For precedent of the fast generation of enaminones from amines and β-ketoesters under CAN catalysis, see: Sridharan, V.; Avendaño, C.; Menéndez, J. C. Synlett 2007, 881.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.