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Volumn 11, Issue 15, 2009, Pages 3302-3305

Secondary amine formation from reductive amination of carbonyl compounds promoted by lewis acid using the InCl3ZEt3SiH system

Author keywords

[No Author keywords available]

Indexed keywords

ALDEHYDE; AMINE; INDIUM; INDIUM CHLORIDE; KETONE; ZINC DERIVATIVE;

EID: 68149131336     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol901111g     Document Type: Article
Times cited : (84)

References (46)
  • 4
    • 0035840229 scopus 로고    scopus 로고
    • For reviews on secondary amine formation, see: a
    • For reviews on secondary amine formation, see: (a) Salvatore, R. N.; Yoon, C. H.; Jung, K. W. Tetrahedron 2001, 57, 7785.
    • (2001) Tetrahedron , vol.57 , pp. 7785
    • Salvatore, R.N.1    Yoon, C.H.2    Jung, K.W.3
  • 10
    • 68149123131 scopus 로고    scopus 로고
    • 4 and Pd-C, see:
    • 4 and Pd-C, see:
  • 14
    • 85068666190 scopus 로고
    • For reviews on the use of sodium cyanoborohydride, see: a
    • For reviews on the use of sodium cyanoborohydride, see: (a) Lane, C. F. Synthesis 1975, 135.
    • (1975) Synthesis , pp. 135
    • Lane, C.F.1
  • 16
  • 17
    • 0025142350 scopus 로고
    • For reviews on the use of sodium triacetoxyborohydride, see: a
    • For reviews on the use of sodium triacetoxyborohydride, see: (a) Abdel-Magid, A. F.; Maryanoff, C. A.; Carson, K. G. Tetrahedron Lett. 1990, 31, 5595.
    • (1990) Tetrahedron Lett , vol.31 , pp. 5595
    • Abdel-Magid, A.F.1    Maryanoff, C.A.2    Carson, K.G.3
  • 23
    • 0037463731 scopus 로고    scopus 로고
    • For recent examples of secondary amine synthesis, see: a
    • For recent examples of secondary amine synthesis, see: (a) Fujita, K,-I.; Li, Z.; Ozeki, N.; Yamaguchi, R. Tetrahedron Lett. 2003, 44, 2687.
    • (2003) Tetrahedron Lett , vol.44 , pp. 2687
    • Fujita, K.-I.1    Li, Z.2    Ozeki, N.3    Yamaguchi, R.4
  • 27
    • 68149135726 scopus 로고    scopus 로고
    • 4-polymethylhydrosiloxane, see: (a) Chandrasekhar, S.; Reddy, C. R.; Ahmed, M. Synlett 2000, 1655.
    • 4-polymethylhydrosiloxane, see: (a) Chandrasekhar, S.; Reddy, C. R.; Ahmed, M. Synlett 2000, 1655.
  • 28
    • 0034624593 scopus 로고    scopus 로고
    • 2)-polymethylhydrosiloxane, see: (b) Hansen, M. C; Buchwald, S. L. Org. Lett. 2000, 2, 713.
    • 2)-polymethylhydrosiloxane, see: (b) Hansen, M. C; Buchwald, S. L. Org. Lett. 2000, 2, 713.
  • 29
    • 0002957731 scopus 로고    scopus 로고
    • 2SnIH, see: (c) Shibata, L; Suwa, T.; Sugiyama, E.; Baba, A. Synlett 1998, 1081.
    • 2SnIH, see: (c) Shibata, L; Suwa, T.; Sugiyama, E.; Baba, A. Synlett 1998, 1081.
  • 32
    • 0001231537 scopus 로고    scopus 로고
    • 3, see: (f) Blackwell, J. M.; Sonmor, E. R.; Scoccitti, T.; Piers, W. Org. Lett. 2000, 2, 3921
    • 3, see: (f) Blackwell, J. M.; Sonmor, E. R.; Scoccitti, T.; Piers, W. Org. Lett. 2000, 2, 3921
  • 33
    • 68149129328 scopus 로고    scopus 로고
    • 2-silica gel, see: (g) Ranu, B. C; Majee, A.; Sarkar, A. J. Org. Chem. 1998, 63, 370.
    • 2-silica gel, see: (g) Ranu, B. C; Majee, A.; Sarkar, A. J. Org. Chem. 1998, 63, 370.
  • 34
    • 0034696035 scopus 로고    scopus 로고
    • 4, see: (h) Saxena, I.; Borah, R.; Sarma, J. C J. Chem. Soc., Perkin Trans. 1 2000, 503.
    • 4, see: (h) Saxena, I.; Borah, R.; Sarma, J. C J. Chem. Soc., Perkin Trans. 1 2000, 503.
  • 38
    • 0033524874 scopus 로고    scopus 로고
    • For examples of the use of Lewis acids in amine synthesis, see: (a) Phanstiel, IV, O, Wang, Q. X, Powell, D. H, Ospina, M. P, Lesson, B. A. J. Org. Chem. 1999, 64, 803
    • For examples of the use of Lewis acids in amine synthesis, see: (a) Phanstiel, IV, O.; Wang, Q. X.; Powell, D. H.; Ospina, M. P.; Lesson, B. A. J. Org. Chem. 1999, 64, 803.
  • 42
    • 68149093523 scopus 로고    scopus 로고
    • When the Lewis acid loading was reduced to 0.3 equiv or lower, poor conversion and product yield were observed.
    • When the Lewis acid loading was reduced to 0.3 equiv or lower, poor conversion and product yield were observed.
  • 45
    • 68149111679 scopus 로고    scopus 로고
    • No desired product was observed with Lewis acids CuBr, CuBr2, Cu(OTf)2, Fe(NO3)3-9H2O, Fe(acac)3, Zn(OAc)2, ZnCl2, ZnI2, Ni(acac)2, and Ni(Cl04)2-6H2O
    • 2O.
  • 46
    • 68149088629 scopus 로고    scopus 로고
    • No partial double bond isomerization was observed when 1e and the Lewis acid were stirred with or without amine, suggesting that the partial double bond isomerization is unlikely to be caused by the Lewis acid itself.
    • No partial double bond isomerization was observed when 1e and the Lewis acid were stirred with or without amine, suggesting that the partial double bond isomerization is unlikely to be caused by the Lewis acid itself.


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