Trapping bicyclic titanacyclopentenes with bis(trichloromethyl) carbonate (BTC): a new method to bicyclic cyclopentenones
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Zongbao Zhao and Yu Ding
Abstract
Bis(trichloromethyl) carbonate is found to trap bicyclic titanacyclopentenes providing a new method for bicyclization of enynes into bicyclic cyclopentenones.
References
For reviews, see:
(a) N. E. Schore, Org. React., 1991, 40, 1 CAS;
(b) N. E. Schore,
in Comprehensive Organic Synthesis,
ed. B. M. Trost and I. Fleming,
Pergamon Press,
Oxford,
1991, vol. 5,
p. 1037 Search PubMedFor recent examples of this reaction, see:
(c) M. Ahmar, C. Locatelli, D. Colombier and B. Cazes, Tetrahedron Lett., 1997, 38, 5281 CrossRefCAS;
(d) L. Jordi, S. Ricart, J. M. Vinas and J. M. Moretó, Organometallics, 1997, 16, 2808 CrossRefCAS.
W. A. Smit, S. L. Kireev, O. M. Nefedov and V. A. Tarasov, Tetrahedron Lett., 1989, 30, 4021 CrossRef.
(a) Y. K. Chung, B. Y. Lee, N. Jeong, M. Hudecek and P. L. Pauson, Organometallics, 1993, 12, 220 CrossRefCAS;
(b) S. Shambayati, W. E. Crowe and S. L. Schreiber, Tetrahedron Lett., 1990, 31, 5289 CrossRefCAS.
There are many natural products that have been synthesized using this protocol. For examples, see:
(a) T. F. Jamison, S. Shambayati, W. E. Crowe and S. L. Schreiber, J. Am. Chem. Soc., 1994, 116, 5505 CrossRefCAS;
(b) J. Tormo, A. Moyamo, M. A. Pericàs and A. Rieca, J. Org. Chem., 1997, 62, 4851 CrossRefCAS;
(c) E. G. Rowley and N. E. Schore, J. Org. Chem., 1992, 57, 6853 CrossRefCAS;
(d) A. L. Veretenov, D. O. Koltun, W. A. Smit and Y. A. Strelenko, Tetrahedron Lett., 1995, 36, 4651 CrossRefCAS.
For Fe, see:
(a) B. E. Eaton and B. Rollman, J. Am. Chem. Soc., 1992, 114, 6245 CrossRefCAS;
(b) A. J. Pearson and R. A. Dubbert, Organometallics, 1994, 13, 1656 CrossRefCASFor Mo and W, see:
(c) T. R. Hoye and J. A. Suriano, J. Am. Chem. Soc., 1993, 115, 1154 CrossRefCAS;
(d) T. R. Hoye and J. A. Suriano, Organometallics, 1992, 11, 2044 CrossRefCASFor Ru, see:
(e) T. Kondo, N. Suzuki, T. Okada and T. Mitsudo, J. Am. Chem. Soc., 1997, 119, 6187 CrossRefCASFor Ni, see:
(f) K. Tamao, K. Kobayashi and Y. Ito, J. Am. Chem. Soc., 1988, 110, 1286 CrossRefCASFor Pd, see:
(g) N. C. Ihle and C. H. Heathcock, J. Org. Chem., 1993, 58, 560 CrossRefCAS;
(h) W. Oppolzer, Pure. Appl. Chem., 1990, 62, 1941 CAS and references cited therein.
(a) E. Negishi, S. J. Holmes, J. M. Tour and J. A. Miller, J. Am. Chem. Soc., 1985, 107, 2568 CrossRefCAS;
(b) E. Negishi, S. J. Holmes, J. M. Tour, J. A. Miller, F. E. Cedarbaum, D. R. Swanson and T. Takahashi, J. Am. Chem. Soc., 1989, 111, 3336 CrossRefCAS.
(a) F. A. Hicks and S. L. Buchwald, J. Am. Chem. Soc., 1996, 118, 11 688 CrossRefCAS;
(b) N. M. Kablaoui, F. A. Hicks and S. L. Buchwald, J. Am. Chem. Soc., 1997, 119, 4424 CrossRefCAS.
(a) Y. Ding, Z. Zhao and C. Zhou, Tetrahedron, 1997, 53, 2899 CrossRefCAS;
(b) Y. Ding and G. Zhao, J. Chem. Soc., Chem. Commun., 1992, 941 RSC.
For an extensive review, see: L. Cotarca, P. Delogu, A. Nardelli and V. Sunjié, Synthesis, 1996, 553 Search PubMed.
In our initial results, we found one case involving the trapping of diselenotitanacycle with BTC. See: R. Kato, H. Kobayashi and A. Kobayashi, Synth. Met., 1991, 41–43, 2093 Search PubMed.
(a) R. B. Grossman and S. L. Buchwald, J. Org. Chem., 1992, 57, 5803 CrossRefCAS;
(b) S. C. Beck, R. B. Grossman and S. L. Buchwald, J. Am. Chem. Soc., 1994, 116, 8593 CrossRefCAS.
K. Miura, M. Funatsu, H. Saito and A. Hosomi, Tetrahedron Lett., 1996, 37, 9059 CrossRefCAS.
Y. Horikawa, M. Watanabe, T. Fujiwara and T. Takeda, J. Am. Chem. Soc., 1997, 119, 1127 CrossRefCAS.
(a) T. V. Rajanbabu, W. A. Nugent, D. F. Taber and P. J. Fagan, J. Am. Chem. Soc., 1988, 110, 7128 CrossRefCAS;
(b) 11b.
(a) P. J. Fagan and W. A. Nugent, J. Am. Chem. Soc., 1988, 110, 2310 CrossRefCAS;
(b) 14a.
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