메뉴 건너뛰기




Volumn 128, Issue 39, 2006, Pages 12973-12980

Dienamine catalysis: Organocatalytic asymmetric γ-amination of α,β-unsaturated aldehydes

Author keywords

[No Author keywords available]

Indexed keywords

AZODICARBOXYLATES; ORGANOCATALYSIS; SECONDARY AMINES; UNSATURATED ALDEHYDES;

EID: 33749527371     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja064637f     Document Type: Article
Times cited : (344)

References (126)
  • 4
    • 33749519513 scopus 로고    scopus 로고
    • special issue on organocatalysis
    • (d) Acc. Chem. Res. 2004, 37, special issue on organocatalysis.
    • (2004) Acc. Chem. Res. , vol.37
  • 5
    • 33746277515 scopus 로고    scopus 로고
    • For reviews, see, for example: (a) Connon, S. J. Chem.-Eur. J. 2006, 12, 5418.
    • (2006) Chem.-Eur. J. , vol.12 , pp. 5418
    • Connon, S.J.1
  • 21
    • 0037366617 scopus 로고    scopus 로고
    • For a review on the use of nucleophilic catalysts in the Baylis-Hillman reaction, see: (a) Basavaiah, D.; Rao, A. J.; Satyanarayana, T. Chem. Rev. 2003, 103, 811.
    • (2003) Chem. Rev. , vol.103 , pp. 811
    • Basavaiah, D.1    Rao, A.J.2    Satyanarayana, T.3
  • 22
    • 22944474675 scopus 로고    scopus 로고
    • For some recent applications of the Baylis-Hillman reaction, see, for example: (b) Krafft, M. E.; Haxell, T. F. N. J. Am. Chem. Soc. 2005, 127, 10168.
    • (2005) J. Am. Chem. Soc. , vol.127 , pp. 10168
    • Krafft, M.E.1    Haxell, T.F.N.2
  • 26
    • 13744263466 scopus 로고    scopus 로고
    • For another recent application of nucleophilic catalysts, see, for example: (f) Mermerian, A. H.; Fu, G. C. Angew. Chem., Int. Ed. 2005, 44, 949.
    • (2005) Angew. Chem., Int. Ed. , vol.44 , pp. 949
    • Mermerian, A.H.1    Fu, G.C.2
  • 39
    • 32844457119 scopus 로고    scopus 로고
    • For some recent feature articles, see, for example: (a) List, B. Chem. Commun. 2006, 819.
    • (2006) Chem. Commun. , pp. 819
    • List, B.1
  • 41
    • 25444470782 scopus 로고    scopus 로고
    • For application of enamine catalysis in Michael additions, see, for example: (c) Chi, Y.; Gellman, S. H. Org. Lett. 2005, 7, 4253.
    • (2005) Org. Lett. , vol.7 , pp. 4253
    • Chi, Y.1    Gellman, S.H.2
  • 51
    • 17144415210 scopus 로고    scopus 로고
    • For application of enamine catalysis in fluorinations, see, for example: (m) Enders, D.; Hüttl, M. R. M. Synlett 2005, 991.
    • (2005) Synlett , pp. 991
    • Enders, D.1    Hüttl, M.R.M.2
  • 63
    • 0141522552 scopus 로고    scopus 로고
    • For application of enamine catalysis in oxygenations, see, for example: (y) Zhong, G. Angew. Chem., Int. Ed. 2003, 42, 4247.
    • (2003) Angew. Chem., Int. Ed. , vol.42 , pp. 4247
    • Zhong, G.1
  • 70
    • 0345825852 scopus 로고    scopus 로고
    • For application of enamine catalysis in alkylations, see, for example: (af) Vignola, N.; List, B. J. Am. Chem. Soc. 2004, 126, 450.
    • (2004) J. Am. Chem. Soc. , vol.126 , pp. 450
    • Vignola, N.1    List, B.2
  • 71
    • 14944346768 scopus 로고    scopus 로고
    • For applications of iminium-ion catalysis in cycloadditions, see, for example: (ag) Kunz, R. K.; MacMillan, D. W. C. J. Am. Chem. Soc. 2005, 127, 3240.
    • (2005) J. Am. Chem. Soc. , vol.127 , pp. 3240
    • Kunz, R.K.1    MacMillan, D.W.C.2
  • 75
    • 24944514433 scopus 로고    scopus 로고
    • For applications of iminium-ion catalysis in Michael reactions, see, for example: (ak) Prieto, A.; Halland, N.; Jørgensen, K. A. Org. Lett. 2005, 7, 3897.
    • (2005) Org. Lett. , vol.7 , pp. 3897
    • Prieto, A.1    Halland, N.2    Jørgensen, K.A.3
  • 94
    • 0242432417 scopus 로고    scopus 로고
    • For the use of dienamines as electron-rich reagents in cycloaddition reactions, see, for example: (a) Huang, Y.; Unni, A. K.; Thadani, A. N.; Rawal, V. H. Nature 2003, 424, 146.
    • (2003) Nature , vol.424 , pp. 146
    • Huang, Y.1    Unni, A.K.2    Thadani, A.N.3    Rawal, V.H.4
  • 99
    • 84981932204 scopus 로고
    • For the use of dienamines as electron-rich nucleophiles, see, for example: (f) Huisman, H. O. Angew. Chem., Int. Ed. Engl. 1971, 10, 450.
    • (1971) Angew. Chem., Int. Ed. Engl. , vol.10 , pp. 450
    • Huisman, H.O.1
  • 110
    • 33749505424 scopus 로고    scopus 로고
    • note
    • The isolated product proved to be unstable upon standing in toluene at room temperature in the presence of 2a, but was stable under the same reaction conditions in the absence of catalyst 2a.
  • 111
    • 33749504654 scopus 로고    scopus 로고
    • note
    • The absolute configuration was determined on the basis of optical rotation comparison. See the Supporting Information for further details.
  • 118
    • 7444257444 scopus 로고    scopus 로고
    • For other mechanistic and computational investigations on organocatalytic aminations, see: (a) Cheong, P. H.-Y.; Houk, K. N. J. Am. Chem. Soc. 2004, 126, 13912.
    • (2004) J. Am. Chem. Soc. , vol.126 , pp. 13912
    • Cheong, P.H.-Y.1    Houk, K.N.2
  • 121


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.