메뉴 건너뛰기




Volumn 47, Issue 35, 2008, Pages 6620-6623

Germanium(II)-mediated reductive Mannich-type reaction of α-bromoketones to N-alkylimines

Author keywords

Amino ketones; Germanium; Imines; Lewis acids; Mannich reaction

Indexed keywords

CHEMICAL BONDS; CHEMICAL REACTIONS; FORMING; NITROGEN COMPOUNDS;

EID: 52449105873     PISSN: 14337851     EISSN: None     Source Type: Journal    
DOI: 10.1002/anie.200800194     Document Type: Article
Times cited : (17)

References (68)
  • 1
    • 85067856671 scopus 로고
    • Selected reviews: A) M. Tramontini
    • Selected reviews: a) M. Tramontini, Synthesis 1973, 703-775;
    • (1973) Synthesis , pp. 703-775
  • 4
    • 0032482080 scopus 로고    scopus 로고
    • Angew. Chem. Int. Ed. 1998, 37, 1044-1070.
    • (1998) Angew. Chem. Int. Ed , vol.37 , pp. 1044-1070
  • 5
    • 0029034741 scopus 로고    scopus 로고
    • Selected examples: a P. Traxler, U. Trinks, E. Buchdunger, H. Mett, T. Meyer, M. Müller, U. Regenass, J. Rösel, N. Lydon, J. Med. Chem. 1995, 38, 2441-2448;
    • Selected examples: a) P. Traxler, U. Trinks, E. Buchdunger, H. Mett, T. Meyer, M. Müller, U. Regenass, J. Rösel, N. Lydon, J. Med. Chem. 1995, 38, 2441-2448;
  • 11
    • 0000862669 scopus 로고    scopus 로고
    • Recent reviews: a
    • Recent reviews: a) S. Kobayashi, H. Ishitani, Chem. Rev. 1999, 99, 1069-1094;
    • (1999) Chem. Rev , vol.99 , pp. 1069-1094
    • Kobayashi, S.1    Ishitani, H.2
  • 13
    • 53249101232 scopus 로고    scopus 로고
    • Selected examples (not included in references [5] and [6]): a) K. Miura, K. Tamaki, T. Nakagawa, A. Hosomi, Angew. Chem. 2000, 112, 2034-2036;
    • Selected examples (not included in references [5] and [6]): a) K. Miura, K. Tamaki, T. Nakagawa, A. Hosomi, Angew. Chem. 2000, 112, 2034-2036;
  • 14
    • 0034595688 scopus 로고    scopus 로고
    • Angew. Chem. Int. Ed. 2000, 39, 1958-1960;
    • (2000) Angew. Chem. Int. Ed , vol.39 , pp. 1958-1960
  • 17
    • 0001209391 scopus 로고    scopus 로고
    • Selected examples of Mannich-type reactions by using silyl enolates derived from ketones: a D. Ferraris, B. Young, T. Dudding, T. Lectka, J. Am. Chem. Soc. 1998, 120, 4548-4549;
    • Selected examples of Mannich-type reactions by using silyl enolates derived from ketones: a) D. Ferraris, B. Young, T. Dudding, T. Lectka, J. Am. Chem. Soc. 1998, 120, 4548-4549;
  • 25
    • 0037028550 scopus 로고    scopus 로고
    • Selected examples of direct catalytic Mannich-type reactions by using ketones: a B. List, P. Pojarliev, W. T. Biller, H. J. Martin, J. Am. Chem. Soc. 2002, 124, 827-833;
    • Selected examples of direct catalytic Mannich-type reactions by using ketones: a) B. List, P. Pojarliev, W. T. Biller, H. J. Martin, J. Am. Chem. Soc. 2002, 124, 827-833;
  • 30
    • 11144333506 scopus 로고    scopus 로고
    • Angew. Chem. Int. Ed. 2004, 43, 6528-6531;
    • (2004) Angew. Chem. Int. Ed , vol.43 , pp. 6528-6531
  • 33
    • 21244473265 scopus 로고    scopus 로고
    • Angew. Chem. Int. Ed. 2005, 44, 4077-4079;
    • (2005) Angew. Chem. Int. Ed , vol.44 , pp. 4077-4079
  • 39
    • 33746255430 scopus 로고    scopus 로고
    • Angew. Chem. Int. Ed. 2006, 45, 3146-3150;
    • (2006) Angew. Chem. Int. Ed , vol.45 , pp. 3146-3150
  • 52
    • 53249132532 scopus 로고    scopus 로고
    • Program: Gaussian 03, Revision C.02. Method:B3PW91. Basis sets: 6-31 + G(d,p). Solvation: PCM with ua0 radii (see the Supporting Information).
    • Program: Gaussian 03, Revision C.02. Method:B3PW91. Basis sets: 6-31 + G(d,p). Solvation: PCM with ua0 radii (see the Supporting Information).
  • 54
    • 2142715741 scopus 로고    scopus 로고
    • 2 in organic synthesis: a G. A. Molander, C. R. Harris, Chem. Rev. 1996, 96, 307-338;
    • 2 in organic synthesis: a) G. A. Molander, C. R. Harris, Chem. Rev. 1996, 96, 307-338;
  • 55
    • 0346787791 scopus 로고    scopus 로고
    • b) H. B. Kagan, Tetrahedron 2003, 59, 10351-10372;
    • (2003) Tetrahedron , vol.59 , pp. 10351-10372
    • Kagan, H.B.1
  • 57
    • 0028285609 scopus 로고
    • For low-valent germanium-mediated reductive C-C bond formation reactions, see; a
    • For low-valent germanium-mediated reductive C-C bond formation reactions, see; a) Y. Hashimoto, H. Kagoshima, K. Saigo, Tetrahedron Lett. 1994, 35, 4805-4808;
    • (1994) Tetrahedron Lett , vol.35 , pp. 4805-4808
    • Hashimoto, Y.1    Kagoshima, H.2    Saigo, K.3
  • 61
    • 0029135125 scopus 로고    scopus 로고
    • 3 catalyst: a) S. Kobayashi, H. Ishitani, S. Nagayama, Synthesis 1995, 1195-1202;
    • 3 catalyst: a) S. Kobayashi, H. Ishitani, S. Nagayama, Synthesis 1995, 1195-1202;
  • 62
  • 63
    • 0037459890 scopus 로고    scopus 로고
    • Selected reviews on the synthesis of substituted piperidines: a P. M. Weintraub, J. S. Sabol, J. M. Kane, D. R. Borcherding, Tetrahedron 2003, 59, 2953-2989;
    • Selected reviews on the synthesis of substituted piperidines: a) P. M. Weintraub, J. S. Sabol, J. M. Kane, D. R. Borcherding, Tetrahedron 2003, 59, 2953-2989;
  • 66
    • 53249147050 scopus 로고    scopus 로고
    • We believe trihalogenated germanium enolates generated from bromoketones and GeCl2/dioxane are the reactive species, and employed 2c as a chemical model for the enolate, see reference [11c
    • 2/dioxane are the reactive species, and employed 2c as a chemical model for the enolate, see reference [11c].
  • 68
    • 53249089988 scopus 로고    scopus 로고
    • When we optimized the adduct 3 f by placing a nitrogen atom in an axial position and an oxygen atom in an equatorial position, the nitrogen center spontaneously returned to an equatorial position during optimization.
    • When we optimized the adduct 3 f by placing a nitrogen atom in an axial position and an oxygen atom in an equatorial position, the nitrogen center spontaneously returned to an equatorial position during optimization.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.