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Volumn 43, Issue 17, 2004, Pages 2206-2225

Beyond thermodynamic acidity: A perspective on the complex-induced proximity effect (CIPE) in deprotonation reactions

Author keywords

Arenes; Heterocycles; Lithiation; Metalation; Reaction mechanisms

Indexed keywords

DATA ACQUISITION; LITHIUM; SYNTHESIS (CHEMICAL); THERMODYNAMIC PROPERTIES;

EID: 3242659209     PISSN: 14337851     EISSN: None     Source Type: Journal    
DOI: 10.1002/anie.200300590     Document Type: Review
Times cited : (662)

References (142)
  • 6
    • 0000490008 scopus 로고
    • A. Eschenmoser, Angew. Chem. 1994, 106, 2455; Angew. Chem. Int. Ed. Engl. 1994, 33, 2363.
    • (1994) Angew. Chem. , vol.106 , pp. 2455
    • Eschenmoser, A.1
  • 7
    • 2242424585 scopus 로고
    • A. Eschenmoser, Angew. Chem. 1994, 106, 2455; Angew. Chem. Int. Ed. Engl. 1994, 33, 2363.
    • (1994) Angew. Chem. Int. Ed. Engl. , vol.33 , pp. 2363
  • 23
    • 0002307974 scopus 로고
    • (Ed.: W. G. Dauben), Robert E. Krieger Publishing Company, Malabar, FL
    • H. W. Gschwend, H. R. Rodriguez in Organic Reactions, Vol. 26 (Ed.: W. G. Dauben), Robert E. Krieger Publishing Company, Malabar, FL, 1979, p. 1.
    • (1979) Organic Reactions , vol.26 , pp. 1
    • Gschwend, H.W.1    Rodriguez, H.R.2
  • 28
    • 4544302930 scopus 로고    scopus 로고
    • Ph.D. Thesis, University of Illinois at Urbana-Champaign
    • Such control is not observed in all cases and can be substrate-dependent; for example, a mixture of 1,2- and 1,4-addition products is obtained upon the addition of the lithiated intermediate of N-Boc-N-(p-methoxyphenyl)cinnamylamine to cyclohexenone: G. A. Weisenburger, Ph.D. Thesis, University of Illinois at Urbana-Champaign, 1998.
    • (1998)
    • Weisenburger, G.A.1
  • 32
    • 33748493881 scopus 로고
    • N. Hommes, P. von R. Schleyer, Angew. Chem. 1992, 104, 768; Angew. Chem. Int. Ed. Engl. 1992, 31, 755.
    • (1992) Angew. Chem. Int. Ed. Engl. , vol.31 , pp. 755
  • 39
    • 0000854142 scopus 로고    scopus 로고
    • b) D. Hoppe, T. Hense, Angew. Chem. 1997, 109, 2376; Angew. Chem. Int. Ed. Engl. 1997, 36, 2282;
    • (1997) Angew. Chem. , vol.109 , pp. 2376
    • Hoppe, D.1    Hense, T.2
  • 40
    • 0030694010 scopus 로고    scopus 로고
    • b) D. Hoppe, T. Hense, Angew. Chem. 1997, 109, 2376; Angew. Chem. Int. Ed. Engl. 1997, 36, 2282;
    • (1997) Angew. Chem. Int. Ed. Engl. , vol.36 , pp. 2282
  • 41
  • 58
    • 0343147529 scopus 로고
    • D. Hoppe, M. Paetow, F. Hintze, Angew. Chem. 1993, 105, 430; Angew. Chem. Int. Ed. Engl. 1993, 32, 394.
    • (1993) Angew. Chem. Int. Ed. Engl. , vol.32 , pp. 394
  • 62
    • 0001386975 scopus 로고
    • For a discussion of the effect of TMEDA in other lithiation reactions, see: D. B. Collum, Acc. Chem. Res. 1992, 25, 448.
    • (1992) Acc. Chem. Res. , vol.25 , pp. 448
    • Collum, D.B.1
  • 68
    • 0026553166 scopus 로고
    • For more recent competition experiments, see: C. Quesnelle, T. Iihama, T. Aubert, H. Perrier, V. Snieckus, Tetrahedron Lett. 1992, 33, 2625; M. Watanabe, M. Date, K. Kawanishi, T. Hori, S. Furnkawa, Chem. Pharm. Bull. 1990, 38, 2637; A. J. Bridges, A. Lee, E. C. Maduakor, C. E. Schwartz, Tetrahedron Lett. 1992, 33, 7495; G. Katsoulos, S. Takagishi, M. Schlosser, Synlett 1991, 731; S. Takagishi, G. Katsoulos, M. Schlosser, Synlett 1992, 360; C. Mukherjee, A. De, Synlett 2002, 325.
    • (1992) Tetrahedron Lett. , vol.33 , pp. 2625
    • Quesnelle, C.1    Iihama, T.2    Aubert, T.3    Perrier, H.4    Snieckus, V.5
  • 69
    • 0025144942 scopus 로고
    • For more recent competition experiments, see: C. Quesnelle, T. Iihama, T. Aubert, H. Perrier, V. Snieckus, Tetrahedron Lett. 1992, 33, 2625; M. Watanabe, M. Date, K. Kawanishi, T. Hori, S. Furnkawa, Chem. Pharm. Bull. 1990, 38, 2637; A. J. Bridges, A. Lee, E. C. Maduakor, C. E. Schwartz, Tetrahedron Lett. 1992, 33, 7495; G. Katsoulos, S. Takagishi, M. Schlosser, Synlett 1991, 731; S. Takagishi, G. Katsoulos, M. Schlosser, Synlett 1992, 360; C. Mukherjee, A. De, Synlett 2002, 325.
    • (1990) Chem. Pharm. Bull. , vol.38 , pp. 2637
    • Watanabe, M.1    Date, M.2    Kawanishi, K.3    Hori, T.4    Furnkawa, S.5
  • 70
    • 0026440023 scopus 로고
    • For more recent competition experiments, see: C. Quesnelle, T. Iihama, T. Aubert, H. Perrier, V. Snieckus, Tetrahedron Lett. 1992, 33, 2625; M. Watanabe, M. Date, K. Kawanishi, T. Hori, S. Furnkawa, Chem. Pharm. Bull. 1990, 38, 2637; A. J. Bridges, A. Lee, E. C. Maduakor, C. E. Schwartz, Tetrahedron Lett. 1992, 33, 7495; G. Katsoulos, S. Takagishi, M. Schlosser, Synlett 1991, 731; S. Takagishi, G. Katsoulos, M. Schlosser, Synlett 1992, 360; C. Mukherjee, A. De, Synlett 2002, 325.
    • (1992) Tetrahedron Lett. , vol.33 , pp. 7495
    • Bridges, A.J.1    Lee, A.2    Maduakor, E.C.3    Schwartz, C.E.4
  • 71
    • 68949112688 scopus 로고
    • For more recent competition experiments, see: C. Quesnelle, T. Iihama, T. Aubert, H. Perrier, V. Snieckus, Tetrahedron Lett. 1992, 33, 2625; M. Watanabe, M. Date, K. Kawanishi, T. Hori, S. Furnkawa, Chem. Pharm. Bull. 1990, 38, 2637; A. J. Bridges, A. Lee, E. C. Maduakor, C. E. Schwartz, Tetrahedron Lett. 1992, 33, 7495; G. Katsoulos, S. Takagishi, M. Schlosser, Synlett 1991, 731; S. Takagishi, G. Katsoulos, M. Schlosser, Synlett 1992, 360; C. Mukherjee, A. De, Synlett 2002, 325.
    • (1991) Synlett , pp. 731
    • Katsoulos, G.1    Takagishi, S.2    Schlosser, M.3
  • 72
    • 80755141140 scopus 로고
    • For more recent competition experiments, see: C. Quesnelle, T. Iihama, T. Aubert, H. Perrier, V. Snieckus, Tetrahedron Lett. 1992, 33, 2625; M. Watanabe, M. Date, K. Kawanishi, T. Hori, S. Furnkawa, Chem. Pharm. Bull. 1990, 38, 2637; A. J. Bridges, A. Lee, E. C. Maduakor, C. E. Schwartz, Tetrahedron Lett. 1992, 33, 7495; G. Katsoulos, S. Takagishi, M. Schlosser, Synlett 1991, 731; S. Takagishi, G. Katsoulos, M. Schlosser, Synlett 1992, 360; C. Mukherjee, A. De, Synlett 2002, 325.
    • (1992) Synlett , pp. 360
    • Takagishi, S.1    Katsoulos, G.2    Schlosser, M.3
  • 73
    • 0036167186 scopus 로고    scopus 로고
    • For more recent competition experiments, see: C. Quesnelle, T. Iihama, T. Aubert, H. Perrier, V. Snieckus, Tetrahedron Lett. 1992, 33, 2625; M. Watanabe, M. Date, K. Kawanishi, T. Hori, S. Furnkawa, Chem. Pharm. Bull. 1990, 38, 2637; A. J. Bridges, A. Lee, E. C. Maduakor, C. E. Schwartz, Tetrahedron Lett. 1992, 33, 7495; G. Katsoulos, S. Takagishi, M. Schlosser, Synlett 1991, 731; S. Takagishi, G. Katsoulos, M. Schlosser, Synlett 1992, 360; C. Mukherjee, A. De, Synlett 2002, 325.
    • (2002) Synlett , pp. 325
    • Mukherjee, C.1    De, A.2
  • 78
    • 0141670408 scopus 로고    scopus 로고
    • b) for deeper structural insight from X-ray and multinuclear NMR studies, see: A. E. H. Wheatley, Eur. J. Inorg. Chem. 2003, 3291; for the impact of DoM on the development of significant new methods of stereocontrol owing to amide atropisomerism, see: J. Clayden, Chem. Commun. 2004, 127.
    • (2003) Eur. J. Inorg. Chem. , pp. 3291
    • Wheatley, A.E.H.1
  • 79
    • 1642520984 scopus 로고    scopus 로고
    • b) for deeper structural insight from X-ray and multinuclear NMR studies, see: A. E. H. Wheatley, Eur. J. Inorg. Chem. 2003, 3291; for the impact of DoM on the development of significant new methods of stereocontrol owing to amide atropisomerism, see: J. Clayden, Chem. Commun. 2004, 127.
    • (2004) Chem. Commun. , pp. 127
    • Clayden, J.1
  • 86
    • 0034674249 scopus 로고    scopus 로고
    • K. B. Wiberg, W. F. Bailey, Angew. Chem. 2000, 112, 2211; Angew. Chem. Int. Ed. 2000, 39, 2127.
    • (2000) Angew. Chem. Int. Ed. , vol.39 , pp. 2127
  • 92
    • 0001173363 scopus 로고    scopus 로고
    • P. E. Eaton, R. G. Daniels, D. Casucci, G. T. Cunkle, P. Engel, J. Org. Chem. 1987, 52, 2100; for CIPE effects with alkyl magnesium amides, see: M.-X. Zhang, P. E. Eaton, Angew. Chem. 2002, 114, 2273; Angew. Chem. Int. Ed. 2002, 41, 2169.
    • (1987) J. Org. Chem. , vol.52 , pp. 2100
    • Eaton, P.E.1    Daniels, R.G.2    Casucci, D.3    Cunkle, G.T.4    Engel, P.5
  • 93
    • 0001173363 scopus 로고    scopus 로고
    • P. E. Eaton, R. G. Daniels, D. Casucci, G. T. Cunkle, P. Engel, J. Org. Chem. 1987, 52, 2100; for CIPE effects with alkyl magnesium amides, see: M.-X. Zhang, P. E. Eaton, Angew. Chem. 2002, 114, 2273; Angew. Chem. Int. Ed. 2002, 41, 2169.
    • (2002) Angew. Chem. , vol.114 , pp. 2273
    • Zhang, M.-X.1    Eaton, P.E.2
  • 94
    • 0037124691 scopus 로고    scopus 로고
    • P. E. Eaton, R. G. Daniels, D. Casucci, G. T. Cunkle, P. Engel, J. Org. Chem. 1987, 52, 2100; for CIPE effects with alkyl magnesium amides, see: M.-X. Zhang, P. E. Eaton, Angew. Chem. 2002, 114, 2273; Angew. Chem. Int. Ed. 2002, 41, 2169.
    • (2002) Angew. Chem. Int. Ed. , vol.41 , pp. 2169
  • 95
  • 96
    • 33748236689 scopus 로고
    • U. P. Spitz, P. E. Eaton, Angew. Chem. 1994, 106, 2263; Angew. Chem. Int. Ed. Engl. 1994, 33, 2220.
    • (1994) Angew. Chem. Int. Ed. Engl. , vol.33 , pp. 2220
  • 106
    • 0037059534 scopus 로고    scopus 로고
    • b) J. Barluenga, R. Gonzalez, F. J. Fananas, M. Yus, F. Foubelo, J. Chem. Soc. Perkin Trans. 1 1994, 1069; for an additional pyrrole synthesis, see: M. A. Jacobson, P. G. Williard J. Org. Chem. 2002, 67, 32.
    • (2002) J. Org. Chem. , vol.67 , pp. 32
    • Jacobson, M.A.1    Williard, P.G.2
  • 111
    • 0029878150 scopus 로고    scopus 로고
    • Ph.D. Thesis, University of Waterloo (Canada)
    • P. A. Brough, S. Fisher, B.-P. Zhao, R. C. Thomas, V. Snieckus, Tetrahedron Lett. 1996, 37, 2915; see also: B.-P. Zhao, Ph.D. Thesis, University of Waterloo (Canada), 1993.
    • (1993)
    • Zhao, B.-P.1
  • 113
    • 0035519381 scopus 로고    scopus 로고
    • J.-I. Yoshida, K. Itami, J. Synth. Org. Chem. Jpn. 2001, 59, 1086; for more recent synthetic applications, see: K. Itami, T. Nokami, Y. Ishimura, K. Mitsudo, T. Kamei, J.-I. Yoshida, J. Am. Chem. Soc. 2001, 123, 11577; K. Itami, K. Mitsudo, A. Nishino, J.-I. Yoshida, J. Org. Chem. 2002, 67, 2645.
    • (2001) J. Synth. Org. Chem. Jpn. , vol.59 , pp. 1086
    • Yoshida, J.-I.1    Itami, K.2
  • 114
    • 0035965684 scopus 로고    scopus 로고
    • J.-I. Yoshida, K. Itami, J. Synth. Org. Chem. Jpn. 2001, 59, 1086; for more recent synthetic applications, see: K. Itami, T. Nokami, Y. Ishimura, K. Mitsudo, T. Kamei, J.-I. Yoshida, J. Am. Chem. Soc. 2001, 123, 11577; K. Itami, K. Mitsudo, A. Nishino, J.-I. Yoshida, J. Org. Chem. 2002, 67, 2645.
    • (2001) J. Am. Chem. Soc. , vol.123 , pp. 11577
    • Itami, K.1    Nokami, T.2    Ishimura, Y.3    Mitsudo, K.4    Kamei, T.5    Yoshida, J.-I.6
  • 115
    • 0037134173 scopus 로고    scopus 로고
    • J.-I. Yoshida, K. Itami, J. Synth. Org. Chem. Jpn. 2001, 59, 1086; for more recent synthetic applications, see: K. Itami, T. Nokami, Y. Ishimura, K. Mitsudo, T. Kamei, J.-I. Yoshida, J. Am. Chem. Soc. 2001, 123, 11577; K. Itami, K. Mitsudo, A. Nishino, J.-I. Yoshida, J. Org. Chem. 2002, 67, 2645.
    • (2002) J. Org. Chem. , vol.67 , pp. 2645
    • Itami, K.1    Mitsudo, K.2    Nishino, A.3    Yoshida, J.-I.4
  • 118
    • 0010584369 scopus 로고
    • 2 gives rise, presumably by the NHLi acting as a DMG, to phenanthridinone and phenanthridine, respectively: a) N. S. Narasimhan, R. H. Alurkar, Indian J. Chem. 1969, 7, 1280;
    • (1969) Indian J. Chem. , vol.7 , pp. 1280
    • Narasimhan, N.S.1    Alurkar, R.H.2
  • 120
    • 4544361364 scopus 로고    scopus 로고
    • unpublished results
    • For the application of DreM to the synthesis of bioactive fluorenones, see: A. V. Kalinin, M. A. Reed, V. Snieckus, unpublished results; W. D. Jones, Jr., F. C. Ciske, Synthesis 1998, 1195.
    • Kalinin, A.V.1    Reed, M.A.2    Snieckus, V.3
  • 121
    • 4544284267 scopus 로고    scopus 로고
    • For the application of DreM to the synthesis of bioactive fluorenones, see: A. V. Kalinin, M. A. Reed, V. Snieckus, unpublished results; W. D. Jones, Jr., F. C. Ciske, Synthesis 1998, 1195.
    • (1998) Synthesis , pp. 1195
    • Jones Jr., W.D.1    Ciske, F.C.2
  • 126
    • 0033577824 scopus 로고    scopus 로고
    • B. A. Chauder, A. V. Kalinin, N. J. Taylor, V. Snieckus, Angew. Chem. 1999, 111, 1528; Angew. Chem. Int. Ed. 1999, 38, 1435.
    • (1999) Angew. Chem. Int. Ed. , vol.38 , pp. 1435
  • 137
    • 0029765094 scopus 로고    scopus 로고
    • M. Gray, B. J. Chapell, N. J. Taylor, V. Snieckus, Angew. Chem. 1996, 108, 1609; Angew. Chem. Int. Ed. Engl. 1996, 35, 1558.
    • (1996) Angew. Chem. Int. Ed. Engl. , vol.35 , pp. 1558
  • 139
    • 4544339195 scopus 로고    scopus 로고
    • Ph.D. Thesis, Queen's University
    • b) S. L. MacNeil, Ph.D. Thesis, Queen's University, 2001.
    • (2001)
    • MacNeil, S.L.1


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