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Volumn 47, Issue 5, 2008, Pages 947-950

Synthesis of α-ketoamides by a molecular-sieves-promoted formal oxidative coupling of aliphatic aldehydes with isocyanides

Author keywords

Isocyanides; Ketoamides; Multicomponent reactions; Nitrones; Ugi reaction

Indexed keywords

ALDEHYDES; AMIDES; AMINES; REACTION KINETICS; SYNTHESIS (CHEMICAL);

EID: 38549088924     PISSN: 14337851     EISSN: None     Source Type: Journal    
DOI: 10.1002/anie.200704840     Document Type: Article
Times cited : (104)

References (69)
  • 3
    • 0001215147 scopus 로고
    • a) J. Gante, Angew. Chem. 1994, 106, 1780-1802;
    • (1994) Angew. Chem , vol.106 , pp. 1780-1802
    • Gante, J.1
  • 6
    • 0001267712 scopus 로고    scopus 로고
    • For a general review on vicinal polycarbonyl compounds, see
    • For a general review on vicinal polycarbonyl compounds, see: M. B. Rubin, R. Gleiter, Chem. Rev. 2000, 100, 1121-1164.
    • (2000) Chem. Rev , vol.100 , pp. 1121-1164
    • Rubin, M.B.1    Gleiter, R.2
  • 17
    • 30744433368 scopus 로고    scopus 로고
    • for an application in natural product synthesis, see: c
    • for an application in natural product synthesis, see: c) J. Chen, X. Chen, M. Bois-Choussy, J. Zhu, J. Am. Chem. Soc. 2006, 128, 87-89.
    • (2006) J. Am. Chem. Soc , vol.128 , pp. 87-89
    • Chen, J.1    Chen, X.2    Bois-Choussy, M.3    Zhu, J.4
  • 26
    • 0037020334 scopus 로고    scopus 로고
    • Angew. Chem. Int. Ed. 2002, 41, 3633-3635;
    • (2002) Angew. Chem. Int. Ed , vol.41 , pp. 3633-3635
  • 28
    • 2242457652 scopus 로고    scopus 로고
    • Angew. Chem. Int. Ed. 2002, 41, 4291-4294;
    • (2002) Angew. Chem. Int. Ed , vol.41 , pp. 4291-4294
  • 30
    • 0037450124 scopus 로고    scopus 로고
    • Angew. Chem. Int. Ed. 2003, 42, 811-814;
    • (2003) Angew. Chem. Int. Ed , vol.42 , pp. 811-814
  • 34
    • 33746238103 scopus 로고    scopus 로고
    • Angew. Chem. Int. Ed. 2006, 45, 3495-3497;
    • (2006) Angew. Chem. Int. Ed , vol.45 , pp. 3495-3497
  • 36
    • 34250857457 scopus 로고    scopus 로고
    • Angew. Chem. Int. Ed. 2007, 46, 2485-2488;
    • (2007) Angew. Chem. Int. Ed , vol.46 , pp. 2485-2488
  • 38
    • 34250838053 scopus 로고    scopus 로고
    • Angew. Chem. Int. Ed. 2007, 46, 3291-3295;
    • (2007) Angew. Chem. Int. Ed , vol.46 , pp. 3291-3295
  • 40
    • 34547403674 scopus 로고    scopus 로고
    • Angew. Chem. Int. Ed. 2007, 46, 5775-5778;
    • (2007) Angew. Chem. Int. Ed , vol.46 , pp. 5775-5778
  • 43
    • 0001134412 scopus 로고    scopus 로고
    • Angew. Chem. Int. Ed. 2000, 39, 3168-3210.
    • (2000) Angew. Chem. Int. Ed , vol.39 , pp. 3168-3210
  • 48
    • 3142743715 scopus 로고    scopus 로고
    • for the use of O-alkyl hydroxylamines in the Ugi 4CR, see: e A. Basso, L. Banfi, G. Guanti, R. Riva, A. Riu, Tetrahedron Lett. 2004, 45, 6109-6111.
    • for the use of O-alkyl hydroxylamines in the Ugi 4CR, see: e) A. Basso, L. Banfi, G. Guanti, R. Riva, A. Riu, Tetrahedron Lett. 2004, 45, 6109-6111.
  • 49
    • 11444270603 scopus 로고    scopus 로고
    • For the use of secondary amines in the Ugi 4CR, see: a D. Bonne, M. Dekhane, J. Zhu, Org. Lett. 2004, 6, 4771-4774;
    • For the use of secondary amines in the Ugi 4CR, see: a) D. Bonne, M. Dekhane, J. Zhu, Org. Lett. 2004, 6, 4771-4774;
  • 51
    • 33746321616 scopus 로고    scopus 로고
    • Angew. Chem. Int. Ed. 2006, 45, 1099-1102;
    • (2006) Angew. Chem. Int. Ed , vol.45 , pp. 1099-1102
  • 53
    • 1842465553 scopus 로고
    • For the insertion of isocyanides into C-O bonds of acetals, see: a
    • For the insertion of isocyanides into C-O bonds of acetals, see: a) H. Pellissier, A. Meou, G. Gil, Tetrahedron Lett. 1986, 27, 2979-2980;
    • (1986) Tetrahedron Lett , vol.27 , pp. 2979-2980
    • Pellissier, H.1    Meou, A.2    Gil, G.3
  • 56
    • 85013905940 scopus 로고
    • See, for example: a
    • See, for example: a) K. Mikami, A. Yoshida, Synlett 1995, 29-31;
    • (1995) Synlett , pp. 29-31
    • Mikami, K.1    Yoshida, A.2
  • 65
    • 38549147371 scopus 로고    scopus 로고
    • 3 = cyclohexyl) in ethanol (which can not be adsorbed by 4-Å MS) should be stirred in the presence of 4-Å MS and MeOH-doped 4-Å MS. We obtained the α-ketoamide in comparable yields from the two experiments, which indicates that the saturation of the pores with MeOH may not be important.
    • 3 = cyclohexyl) in ethanol (which can not be adsorbed by 4-Å MS) should be stirred in the presence of 4-Å MS and MeOH-doped 4-Å MS. We obtained the α-ketoamide in comparable yields from the two experiments, which indicates that the saturation of the pores with MeOH may not be important.
  • 66
    • 36149000925 scopus 로고    scopus 로고
    • For the direct formation of an amide from an aldehyde and an amine, see: a
    • For the direct formation of an amide from an aldehyde and an amine, see: a) H. U. Vora, T. Rovis, J. Am. Chem. Soc. 2007, 129, 13796-13797;
    • (2007) J. Am. Chem. Soc , vol.129 , pp. 13796-13797
    • Vora, H.U.1    Rovis, T.2
  • 68
    • 84890597202 scopus 로고    scopus 로고
    • Eds, J. Zhu, H. Bienaymé, Wiley-VCH, Weinheim
    • Multicomponent Reactions (Eds.: J. Zhu, H. Bienaymé), Wiley-VCH, Weinheim, 2005.
    • (2005) Multicomponent Reactions
  • 69
    • 18744384947 scopus 로고    scopus 로고
    • For the one-pot oxidative homologation of aldehydes, see
    • For the one-pot oxidative homologation of aldehydes, see: D. Bonne, M. Dekhane, J. Zhu, J. Am. Chem. Soc. 2005, 127, 6926-6927.
    • (2005) J. Am. Chem. Soc , vol.127 , pp. 6926-6927
    • Bonne, D.1    Dekhane, M.2    Zhu, J.3


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.