Synthesis of carbocycles by insertion of 1,1-dihalo-1-lithio species into zirconacycles
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Nicolas Vicart and Richard J. Whitby
Abstract
1,1-Dihalo-1-lithio species (halogenocarbenoids) undergo double insertion into the carbon–zirconium bonds of a zirconacyclopent-ane or -ene to produce, after hydrolysis, bicyclo[3.3.0]oct-anes and -enes.
References
C. Rousset, D. Swanson, F. Lamaty and E.-I. Negishi, Tetrahedron Lett., 1989, 30, 5105 CrossRefCAS.
E.-I. Negishi, in Comprehensive Organic Synthesis, ed. B. M. Trost and I. Fleming, Pergamon, Oxford, 1991, vol. 5, p. 1163 Search PubMed; R. D. Broene, in Comprehensive Organometallic Chemistry II, ed. E. W. Abel, F. G. A. Stone and G. Wilkinson, Pergamon, Oxford, 1995, vol. 12, p. 323 Search PubMed; N. Uesaka, M. Mori, K. Okamura and T. Date, J. Org. Chem., 1994, 59, 4542 Search PubMed; M. I. Kemp, R. J. Whitby and S. J. Coote, Synthesis, 1998, 557 Search PubMed; E.-I. Negishi, S. M. Ma, T. Sugihara and Y. Noda, J. Org. Chem., 1997, 62, 1922 CrossRefCAS.
C. J. Rousset, D. R. Swanson, F. Lamaty and E.-I. Negishi, Tetrahedron Lett., 1989, 30, 5105 CrossRefCAS; E.-I. Negishi, S. J. Holmes, J. M. Tour, J. A. Miller, F. E. Cedrebaum, D. R. Swanson and T. Takahashi, J. Am. Chem. Soc., 1989, 111, 3336 CrossRefCAS.
(a) J. M. Davis, R. J. Whitby and A. Jaxa-Chamiec, Synlett, 1994, 110 CrossRefCAS;
(b) G. D. Probert, R. J. Whitby and S. J. Coote, Tetrahedron Lett., 1995, 36, 4113 CrossRefCAS and references cited therein..
G. J. Gordon and R. J. Whitby, Chem. Commun., 1997, 1321 RSC.
T. Takahashi, Z. Xi, M. Kotora, C. Xi and K. Nakajima, Tetrahedron Lett., 1996, 37, 7521 CrossRefCAS; T. Takahashi, W. Sun, C. Xi and M. Kotora, Chem. Commun., 1997, 2069 RSC; M. Kotora, C. Xi and T. Takahashi, Tetrahedron Lett., 1998, 39, 4321 CrossRefCAS.
S. F. Fillery, G. J. Gordon, T. Luker and R. J. Whitby, Pure Appl. Chem., 1997, 69, 633 CrossRefCAS and references cited therein..
J. Villieras and M. Rambaud, Synthesis, 1980, 644 CrossRefCAS.
E.-I. Negishi, K. Akiyoshi, B. O'Conner, K. Takagi and G. Wu, J. Am. Chem. Soc., 1989, 111, 3089 CrossRefCAS.
P. Kocienski and C. Barber, Pure Appl. Chem., 1990, 62, 1933 CAS.
G. Erker, R. Petrenz, C. Kruger, F. Lutz, A. Weiss and S. Werner, Organometallics, 1992, 11, 1646 CrossRefCAS; T. Takahashi, Z. Xi, R. Fischer, S. Huo, C. Xi and K. Nakajima, J. Am. Chem. Soc., 1997, 119, 4561 CrossRefCAS; K. Kasai, Y. H. Liu, R. Hara and T. Takahashi, Chem. Commun., 1998, 1989 RSC.
G. L. Larson and O. Rosario, J. Organomet. Chem., 1979, 168, 13 CrossRefCAS.