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Volumn 5, Issue 5, 1999, Pages 1534-1543

Density functional studies on conjugate addition of (Me2CuLi)2 to cyclohexenone: Stereoselectivity and rate-determining step

Author keywords

Conjugate additions; Cuprates; Density functional calculations; Enones

Indexed keywords

2 CYCLOHEXENONE; COPPER; LITHIUM;

EID: 0032943231     PISSN: 09476539     EISSN: None     Source Type: Journal    
DOI: 10.1002/(sici)1521-3765(19990503)5:5<1534::aid-chem1534>3.0.co;2-v     Document Type: Article
Times cited : (78)

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    • Bürgi, H.B.1    Dunitz, J.D.2
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    • note
    • 3, respectively: a) 2-cyclohexenone δ = 208.5, 135.4, 154.4; b) CPcl δ = 227.2, 90.5, 93.4; c) CPop δ = 189.2, 94.9, 75.8.
  • 94
    • 0346923266 scopus 로고    scopus 로고
    • note
    • - in c.
  • 98
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    • For pertinent references on cyanocuprates, see: a) S. H. Bertz, K. Nilsson, K. Ö. Davidson, J. P. Snyder, Angew. Chem. 1998, 110, 327-331; Angew. Chem. Int. Ed. 1998, 37, 314-317;
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    • E. Nakamura, I. Kuwajima, J. Am. Chem. Soc. 1984, 106, 3368-3370; Y. Horiguchi, S. Matsuzawa, E. Nakamura, I. Kuwajima, Tetrahedron Lett. 1986, 27, 4025-4028; E. Nakamura, S. Matsuzawa, Y. Horiguchi, I. Kuwajima, Tetrahedron Lett. 1986, 27, 4029-4032; S. Matsuzawa, Y. Horiguchi, E. Nakamura, I. Kuwajima, Tetrahedron Lett. 1989, 45, 349-362.
    • (1984) J. Am. Chem. Soc. , vol.106 , pp. 3368-3370
    • Nakamura, E.1    Kuwajima, I.2
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    • E. Nakamura, I. Kuwajima, J. Am. Chem. Soc. 1984, 106, 3368-3370; Y. Horiguchi, S. Matsuzawa, E. Nakamura, I. Kuwajima, Tetrahedron Lett. 1986, 27, 4025-4028; E. Nakamura, S. Matsuzawa, Y. Horiguchi, I. Kuwajima, Tetrahedron Lett. 1986, 27, 4029-4032; S. Matsuzawa, Y. Horiguchi, E. Nakamura, I. Kuwajima, Tetrahedron Lett. 1989, 45, 349-362.
    • (1986) Tetrahedron Lett. , vol.27 , pp. 4025-4028
    • Horiguchi, Y.1    Matsuzawa, S.2    Nakamura, E.3    Kuwajima, I.4
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    • E. Nakamura, I. Kuwajima, J. Am. Chem. Soc. 1984, 106, 3368-3370; Y. Horiguchi, S. Matsuzawa, E. Nakamura, I. Kuwajima, Tetrahedron Lett. 1986, 27, 4025-4028; E. Nakamura, S. Matsuzawa, Y. Horiguchi, I. Kuwajima, Tetrahedron Lett. 1986, 27, 4029-4032; S. Matsuzawa, Y. Horiguchi, E. Nakamura, I. Kuwajima, Tetrahedron Lett. 1989, 45, 349-362.
    • (1986) Tetrahedron Lett. , vol.27 , pp. 4029-4032
    • Nakamura, E.1    Matsuzawa, S.2    Horiguchi, Y.3    Kuwajima, I.4
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    • E. Nakamura, I. Kuwajima, J. Am. Chem. Soc. 1984, 106, 3368-3370; Y. Horiguchi, S. Matsuzawa, E. Nakamura, I. Kuwajima, Tetrahedron Lett. 1986, 27, 4025-4028; E. Nakamura, S. Matsuzawa, Y. Horiguchi, I. Kuwajima, Tetrahedron Lett. 1986, 27, 4029-4032; S. Matsuzawa, Y. Horiguchi, E. Nakamura, I. Kuwajima, Tetrahedron Lett. 1989, 45, 349-362.
    • (1989) Tetrahedron Lett. , vol.45 , pp. 349-362
    • Matsuzawa, S.1    Horiguchi, Y.2    Nakamura, E.3    Kuwajima, I.4
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    • See also: E. J. Corey, N. W. Boaz, Tetrahedron Lett, 1985, 26, 6015-6018; E. J. Corey, N. W. Boaz, Tetrahedron Lett, 1985, 26, 6019-6022; A. Alexakis, J. Berlan, Y. Besace, Tetrahedron Lett. 1986, 27, 1047-1050; review: E. Nakamura, Organocopper Reagents (Ed.: R. J. K. Taylor), Oxford University Press, 1994, Chapter 6, pp. 129-142.
    • (1985) Tetrahedron Lett , vol.26 , pp. 6015-6018
    • Corey, E.J.1    Boaz, N.W.2
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    • See also: E. J. Corey, N. W. Boaz, Tetrahedron Lett, 1985, 26, 6015-6018; E. J. Corey, N. W. Boaz, Tetrahedron Lett, 1985, 26, 6019-6022; A. Alexakis, J. Berlan, Y. Besace, Tetrahedron Lett. 1986, 27, 1047-1050; review: E. Nakamura, Organocopper Reagents (Ed.: R. J. K. Taylor), Oxford University Press, 1994, Chapter 6, pp. 129-142.
    • (1985) Tetrahedron Lett , vol.26 , pp. 6019-6022
    • Corey, E.J.1    Boaz, N.W.2
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    • See also: E. J. Corey, N. W. Boaz, Tetrahedron Lett, 1985, 26, 6015-6018; E. J. Corey, N. W. Boaz, Tetrahedron Lett, 1985, 26, 6019-6022; A. Alexakis, J. Berlan, Y. Besace, Tetrahedron Lett. 1986, 27, 1047-1050; review: E. Nakamura, Organocopper Reagents (Ed.: R. J. K. Taylor), Oxford University Press, 1994, Chapter 6, pp. 129-142.
    • (1986) Tetrahedron Lett. , vol.27 , pp. 1047-1050
    • Alexakis, A.1    Berlan, J.2    Besace, Y.3
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    • (Ed.: R. J. K. Taylor), Oxford University Press, Chapter 6
    • See also: E. J. Corey, N. W. Boaz, Tetrahedron Lett, 1985, 26, 6015-6018; E. J. Corey, N. W. Boaz, Tetrahedron Lett, 1985, 26, 6019-6022; A. Alexakis, J. Berlan, Y. Besace, Tetrahedron Lett. 1986, 27, 1047-1050; review: E. Nakamura, Organocopper Reagents (Ed.: R. J. K. Taylor), Oxford University Press, 1994, Chapter 6, pp. 129-142.
    • (1994) Organocopper Reagents , pp. 129-142
    • Nakamura, E.1
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    • B. L. Feringa, M. Pineschi, L. A. Arnold, R. Imbos, A. H. M. de Vries, Angew. Chem. 1997, 109, 2733-2736; Angew. Chem. Int. Ed. Engl. 1997, 36, 2620-2623; A. K. H. Knoobel, I. H. Escher, A. Pfaltz, Synlett 1997, 1429-1431; Y. Nakagawa, M. Kanai, Y. Nagaoka, K. Tomioka, Tetrahedron 1998, 54, 10295-10307.
    • (1997) Angew. Chem. , vol.109 , pp. 2733-2736
    • Feringa, B.L.1    Pineschi, M.2    Arnold, L.A.3    Imbos, R.4    De Vries, A.H.M.5
  • 109
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    • B. L. Feringa, M. Pineschi, L. A. Arnold, R. Imbos, A. H. M. de Vries, Angew. Chem. 1997, 109, 2733-2736; Angew. Chem. Int. Ed. Engl. 1997, 36, 2620-2623; A. K. H. Knoobel, I. H. Escher, A. Pfaltz, Synlett 1997, 1429-1431; Y. Nakagawa, M. Kanai, Y. Nagaoka, K. Tomioka, Tetrahedron 1998, 54, 10295-10307.
    • (1997) Angew. Chem. Int. Ed. Engl. , vol.36 , pp. 2620-2623
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    • B. L. Feringa, M. Pineschi, L. A. Arnold, R. Imbos, A. H. M. de Vries, Angew. Chem. 1997, 109, 2733-2736; Angew. Chem. Int. Ed. Engl. 1997, 36, 2620-2623; A. K. H. Knoobel, I. H. Escher, A. Pfaltz, Synlett 1997, 1429-1431; Y. Nakagawa, M. Kanai, Y. Nagaoka, K. Tomioka, Tetrahedron 1998, 54, 10295-10307.
    • (1997) Synlett , pp. 1429-1431
    • Knoobel, A.K.H.1    Escher, I.H.2    Pfaltz, A.3
  • 111
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    • B. L. Feringa, M. Pineschi, L. A. Arnold, R. Imbos, A. H. M. de Vries, Angew. Chem. 1997, 109, 2733-2736; Angew. Chem. Int. Ed. Engl. 1997, 36, 2620-2623; A. K. H. Knoobel, I. H. Escher, A. Pfaltz, Synlett 1997, 1429-1431; Y. Nakagawa, M. Kanai, Y. Nagaoka, K. Tomioka, Tetrahedron 1998, 54, 10295-10307.
    • (1998) Tetrahedron , vol.54 , pp. 10295-10307
    • Nakagawa, Y.1    Kanai, M.2    Nagaoka, Y.3    Tomioka, K.4


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