Diastereoselective synthesis of highly substituted five-membered-ring oxygen heterocycles by zirconocene-mediated C - C coupling reactions

Angewandte Chemie - International Edition

Volumn 37, Issue 12, 1998, Pages 1673-1675

  Enders, Dieter ^a   Kroll, Manfred ^a   Raabe, Gerhard ^a   Runsink, Jan ^a  

^a RWTH AACHEN UNIVERSITY   (Germany)

Author keywords

Asymmetric syntheses; Heterocycles; Homoenolates; Insertions; Zirconium

Indexed keywords

EID: 0032479386     PISSN: 14337851     EISSN: None     Source Type: Journal    
DOI: 10.1002/(SICI)1521-3773(19980703)37:12<1673::AID-ANIE1673>3.0.CO;2-A     Document Type: Article

References (44)

1. L. S. Hegedus, Transition Metals in the Synthesis of Complex Organic Molecules, University Science Books, Mill Valley, CA, 1994.
2. The chemistry of zirconocene: a) E.-I. Negishi, D. Y. Kondakov, Chem. Soc. Rev. 1996, 417; b) A. H. Hoveyda, J. P. Morken, Angew. Chem. 1996, 108, 1379; Angew. Chem. Int. Ed. Engl. 1996, 35, 1262; c) E. M. Page, S. A. Wass, Coord. Chem. Rev. 1996, 152, 411; d) Y. Hanzawa, H. Ito, T. Taguchi, Synlett 1995, 299; e) M. E. Maier, Nachr. Chem. Tech. Lab. 1993, 41, 811; f) E.-I. Negishi, T. Takahashi, Reviews on Heteroatom Chemistry 1992, 6, 177; g) H. Yasuda, A. Nakamura, Angew. Chem. 1981, 99, 745; Angew. Chem. Int. Ed. Engl. 1987, 26, 723. Insertion of ketones into (butadiene)zirconocenes: L. López, M. Berlekamp, D. Kowalski, G. Erker. Angew. Chem. 1994, 106, 1168; Angew. Chem. Int. Ed. Engl. 1994, 33, 1114.
3. The chemistry of zirconocene: a) E.-I. Negishi, D. Y. Kondakov, Chem. Soc. Rev. 1996, 417; b) A. H. Hoveyda, J. P. Morken, Angew. Chem. 1996, 108, 1379; Angew. Chem. Int. Ed. Engl. 1996, 35, 1262; c) E. M. Page, S. A. Wass, Coord. Chem. Rev. 1996, 152, 411; d) Y. Hanzawa, H. Ito, T. Taguchi, Synlett 1995, 299; e) M. E. Maier, Nachr. Chem. Tech. Lab. 1993, 41, 811; f) E.-I. Negishi, T. Takahashi, Reviews on Heteroatom Chemistry 1992, 6, 177; g) H. Yasuda, A. Nakamura, Angew. Chem. 1981, 99, 745; Angew. Chem. Int. Ed. Engl. 1987, 26, 723. Insertion of ketones into (butadiene)zirconocenes: L. López, M. Berlekamp, D. Kowalski, G. Erker. Angew. Chem. 1994, 106, 1168; Angew. Chem. Int. Ed. Engl. 1994, 33, 1114.
4. The chemistry of zirconocene: a) E.-I. Negishi, D. Y. Kondakov, Chem. Soc. Rev. 1996, 417; b) A. H. Hoveyda, J. P. Morken, Angew. Chem. 1996, 108, 1379; Angew. Chem. Int. Ed. Engl. 1996, 35, 1262; c) E. M. Page, S. A. Wass, Coord. Chem. Rev. 1996, 152, 411; d) Y. Hanzawa, H. Ito, T. Taguchi, Synlett 1995, 299; e) M. E. Maier, Nachr. Chem. Tech. Lab. 1993, 41, 811; f) E.-I. Negishi, T. Takahashi, Reviews on Heteroatom Chemistry 1992, 6, 177; g) H. Yasuda, A. Nakamura, Angew. Chem. 1981, 99, 745; Angew. Chem. Int. Ed. Engl. 1987, 26, 723. Insertion of ketones into (butadiene)zirconocenes: L. López, M. Berlekamp, D. Kowalski, G. Erker. Angew. Chem. 1994, 106, 1168; Angew. Chem. Int. Ed. Engl. 1994, 33, 1114.
5. The chemistry of zirconocene: a) E.-I. Negishi, D. Y. Kondakov, Chem. Soc. Rev. 1996, 417; b) A. H. Hoveyda, J. P. Morken, Angew. Chem. 1996, 108, 1379; Angew. Chem. Int. Ed. Engl. 1996, 35, 1262; c) E. M. Page, S. A. Wass, Coord. Chem. Rev. 1996, 152, 411; d) Y. Hanzawa, H. Ito, T. Taguchi, Synlett 1995, 299; e) M. E. Maier, Nachr. Chem. Tech. Lab. 1993, 41, 811; f) E.-I. Negishi, T. Takahashi, Reviews on Heteroatom Chemistry 1992, 6, 177; g) H. Yasuda, A. Nakamura, Angew. Chem. 1981, 99, 745; Angew. Chem. Int. Ed. Engl. 1987, 26, 723. Insertion of ketones into (butadiene)zirconocenes: L. López, M. Berlekamp, D. Kowalski, G. Erker. Angew. Chem. 1994, 106, 1168; Angew. Chem. Int. Ed. Engl. 1994, 33, 1114.
6. The chemistry of zirconocene: a) E.-I. Negishi, D. Y. Kondakov, Chem. Soc. Rev. 1996, 417; b) A. H. Hoveyda, J. P. Morken, Angew. Chem. 1996, 108, 1379; Angew. Chem. Int. Ed. Engl. 1996, 35, 1262; c) E. M. Page, S. A. Wass, Coord. Chem. Rev. 1996, 152, 411; d) Y. Hanzawa, H. Ito, T. Taguchi, Synlett 1995, 299; e) M. E. Maier, Nachr. Chem. Tech. Lab. 1993, 41, 811; f) E.-I. Negishi, T. Takahashi, Reviews on Heteroatom Chemistry 1992, 6, 177; g) H. Yasuda, A. Nakamura, Angew. Chem. 1981, 99, 745; Angew. Chem. Int. Ed. Engl. 1987, 26, 723. Insertion of ketones into (butadiene)zirconocenes: L. López, M. Berlekamp, D. Kowalski, G. Erker. Angew. Chem. 1994, 106, 1168; Angew. Chem. Int. Ed. Engl. 1994, 33, 1114.
7. The chemistry of zirconocene: a) E.-I. Negishi, D. Y. Kondakov, Chem. Soc. Rev. 1996, 417; b) A. H. Hoveyda, J. P. Morken, Angew. Chem. 1996, 108, 1379; Angew. Chem. Int. Ed. Engl. 1996, 35, 1262; c) E. M. Page, S. A. Wass, Coord. Chem. Rev. 1996, 152, 411; d) Y. Hanzawa, H. Ito, T. Taguchi, Synlett 1995, 299; e) M. E. Maier, Nachr. Chem. Tech. Lab. 1993, 41, 811; f) E.-I. Negishi, T. Takahashi, Reviews on Heteroatom Chemistry 1992, 6, 177; g) H. Yasuda, A. Nakamura, Angew. Chem. 1981, 99, 745; Angew. Chem. Int. Ed. Engl. 1987, 26, 723. Insertion of ketones into (butadiene)zirconocenes: L. López, M. Berlekamp, D. Kowalski, G. Erker. Angew. Chem. 1994, 106, 1168; Angew. Chem. Int. Ed. Engl. 1994, 33, 1114.
8. The chemistry of zirconocene: a) E.-I. Negishi, D. Y. Kondakov, Chem. Soc. Rev. 1996, 417; b) A. H. Hoveyda, J. P. Morken, Angew. Chem. 1996, 108, 1379; Angew. Chem. Int. Ed. Engl. 1996, 35, 1262; c) E. M. Page, S. A. Wass, Coord. Chem. Rev. 1996, 152, 411; d) Y. Hanzawa, H. Ito, T. Taguchi, Synlett 1995, 299; e) M. E. Maier, Nachr. Chem. Tech. Lab. 1993, 41, 811; f) E.-I. Negishi, T. Takahashi, Reviews on Heteroatom Chemistry 1992, 6, 177; g) H. Yasuda, A. Nakamura, Angew. Chem. 1981, 99, 745; Angew. Chem. Int. Ed. Engl. 1987, 26, 723. Insertion of ketones into (butadiene)zirconocenes: L. López, M. Berlekamp, D. Kowalski, G. Erker. Angew. Chem. 1994, 106, 1168; Angew. Chem. Int. Ed. Engl. 1994, 33, 1114.
9. The chemistry of zirconocene: a) E.-I. Negishi, D. Y. Kondakov, Chem. Soc. Rev. 1996, 417; b) A. H. Hoveyda, J. P. Morken, Angew. Chem. 1996, 108, 1379; Angew. Chem. Int. Ed. Engl. 1996, 35, 1262; c) E. M. Page, S. A. Wass, Coord. Chem. Rev. 1996, 152, 411; d) Y. Hanzawa, H. Ito, T. Taguchi, Synlett 1995, 299; e) M. E. Maier, Nachr. Chem. Tech. Lab. 1993, 41, 811; f) E.-I. Negishi, T. Takahashi, Reviews on Heteroatom Chemistry 1992, 6, 177; g) H. Yasuda, A. Nakamura, Angew. Chem. 1981, 99, 745; Angew. Chem. Int. Ed. Engl. 1987, 26, 723. Insertion of ketones into (butadiene)zirconocenes: L. López, M. Berlekamp, D. Kowalski, G. Erker. Angew. Chem. 1994, 106, 1168; Angew. Chem. Int. Ed. Engl. 1994, 33, 1114.
10. The chemistry of zirconocene: a) E.-I. Negishi, D. Y. Kondakov, Chem. Soc. Rev. 1996, 417; b) A. H. Hoveyda, J. P. Morken, Angew. Chem. 1996, 108, 1379; Angew. Chem. Int. Ed. Engl. 1996, 35, 1262; c) E. M. Page, S. A. Wass, Coord. Chem. Rev. 1996, 152, 411; d) Y. Hanzawa, H. Ito, T. Taguchi, Synlett 1995, 299; e) M. E. Maier, Nachr. Chem. Tech. Lab. 1993, 41, 811; f) E.-I. Negishi, T. Takahashi, Reviews on Heteroatom Chemistry 1992, 6, 177; g) H. Yasuda, A. Nakamura, Angew. Chem. 1981, 99, 745; Angew. Chem. Int. Ed. Engl. 1987, 26, 723. Insertion of ketones into (butadiene)zirconocenes: L. López, M. Berlekamp, D. Kowalski, G. Erker. Angew. Chem. 1994, 106, 1168; Angew. Chem. Int. Ed. Engl. 1994, 33, 1114.
11. The chemistry of zirconocene: a) E.-I. Negishi, D. Y. Kondakov, Chem. Soc. Rev. 1996, 417; b) A. H. Hoveyda, J. P. Morken, Angew. Chem. 1996, 108, 1379; Angew. Chem. Int. Ed. Engl. 1996, 35, 1262; c) E. M. Page, S. A. Wass, Coord. Chem. Rev. 1996, 152, 411; d) Y. Hanzawa, H. Ito, T. Taguchi, Synlett 1995, 299; e) M. E. Maier, Nachr. Chem. Tech. Lab. 1993, 41, 811; f) E.-I. Negishi, T. Takahashi, Reviews on Heteroatom Chemistry 1992, 6, 177; g) H. Yasuda, A. Nakamura, Angew. Chem. 1981, 99, 745; Angew. Chem. Int. Ed. Engl. 1987, 26, 723. Insertion of ketones into (butadiene)zirconocenes: L. López, M. Berlekamp, D. Kowalski, G. Erker. Angew. Chem. 1994, 106, 1168; Angew. Chem. Int. Ed. Engl. 1994, 33, 1114.
12. The chemistry of zirconocene: a) E.-I. Negishi, D. Y. Kondakov, Chem. Soc. Rev. 1996, 417; b) A. H. Hoveyda, J. P. Morken, Angew. Chem. 1996, 108, 1379; Angew. Chem. Int. Ed. Engl. 1996, 35, 1262; c) E. M. Page, S. A. Wass, Coord. Chem. Rev. 1996, 152, 411; d) Y. Hanzawa, H. Ito, T. Taguchi, Synlett 1995, 299; e) M. E. Maier, Nachr. Chem. Tech. Lab. 1993, 41, 811; f) E.-I. Negishi, T. Takahashi, Reviews on Heteroatom Chemistry 1992, 6, 177; g) H. Yasuda, A. Nakamura, Angew. Chem. 1981, 99, 745; Angew. Chem. Int. Ed. Engl. 1987, 26, 723. Insertion of ketones into (butadiene)zirconocenes: L. López, M. Berlekamp, D. Kowalski, G. Erker. Angew. Chem. 1994, 106, 1168; Angew. Chem. Int. Ed. Engl. 1994, 33, 1114.
13. For new developments in the field of catalysis see also a) M. S. Visser, N. M. Heron, M. T. Didiuk, J. F. Sagal, A. M. Hoveyda, J. Am. Chem. Soc. 1996, 118, 4291; b) E.-I. Negishi, D. Y. Kondakov, D. Choueiry, K. Kasai, T. Takahashi, J. Am. Chem. Soc. 1996, 118, 9577.
14. For new developments in the field of catalysis see also a) M. S. Visser, N. M. Heron, M. T. Didiuk, J. F. Sagal, A. M. Hoveyda, J. Am. Chem. Soc. 1996, 118, 4291; b) E.-I. Negishi, D. Y. Kondakov, D. Choueiry, K. Kasai, T. Takahashi, J. Am. Chem. Soc. 1996, 118, 9577.
15. Zirconocene imine complexes: a) J. Barluenga, R. Sanz, F. J. Fananás, J. Org. Chem. 1997, 62, 5953; b) D. A. Gately, J. R. Norton, J. Am. Chem. Soc. 1996, 118, 3479, and references therein; c) C. Lefeber, P. Arndt, A. Tillack, W. Baumann, R. Kempe, V. V. Burlakov, U. Rosenthal, Organometallics 1995, 14, 3090; d) M. C. J. Harris, R. J. Whitby, Tetrahedron Lett. 1995, 36, 4287, and references therein; c) R. B. Grossman, W. M. Davis, S. L. Buchwald, J. Am. Chem. Soc. 1991, 113, 2321; f) M. Jensen, T. Livinghouse, J. Am. Chem. Soc. 1989, 111, 4495.
16. Zirconocene imine complexes: a) J. Barluenga, R. Sanz, F. J. Fananás, J. Org. Chem. 1997, 62, 5953; b) D. A. Gately, J. R. Norton, J. Am. Chem. Soc. 1996, 118, 3479, and references therein; c) C. Lefeber, P. Arndt, A. Tillack, W. Baumann, R. Kempe, V. V. Burlakov, U. Rosenthal, Organometallics 1995, 14, 3090; d) M. C. J. Harris, R. J. Whitby, Tetrahedron Lett. 1995, 36, 4287, and references therein; c) R. B. Grossman, W. M. Davis, S. L. Buchwald, J. Am. Chem. Soc. 1991, 113, 2321; f) M. Jensen, T. Livinghouse, J. Am. Chem. Soc. 1989, 111, 4495.
17. Zirconocene imine complexes: a) J. Barluenga, R. Sanz, F. J. Fananás, J. Org. Chem. 1997, 62, 5953; b) D. A. Gately, J. R. Norton, J. Am. Chem. Soc. 1996, 118, 3479, and references therein; c) C. Lefeber, P. Arndt, A. Tillack, W. Baumann, R. Kempe, V. V. Burlakov, U. Rosenthal, Organometallics 1995, 14, 3090; d) M. C. J. Harris, R. J. Whitby, Tetrahedron Lett. 1995, 36, 4287, and references therein; c) R. B. Grossman, W. M. Davis, S. L. Buchwald, J. Am. Chem. Soc. 1991, 113, 2321; f) M. Jensen, T. Livinghouse, J. Am. Chem. Soc. 1989, 111, 4495.
18. Zirconocene imine complexes: a) J. Barluenga, R. Sanz, F. J. Fananás, J. Org. Chem. 1997, 62, 5953; b) D. A. Gately, J. R. Norton, J. Am. Chem. Soc. 1996, 118, 3479, and references therein; c) C. Lefeber, P. Arndt, A. Tillack, W. Baumann, R. Kempe, V. V. Burlakov, U. Rosenthal, Organometallics 1995, 14, 3090; d) M. C. J. Harris, R. J. Whitby, Tetrahedron Lett. 1995, 36, 4287, and references therein; c) R. B. Grossman, W. M. Davis, S. L. Buchwald, J. Am. Chem. Soc. 1991, 113, 2321; f) M. Jensen, T. Livinghouse, J. Am. Chem. Soc. 1989, 111, 4495.
19. Zirconocene imine complexes: a) J. Barluenga, R. Sanz, F. J. Fananás, J. Org. Chem. 1997, 62, 5953; b) D. A. Gately, J. R. Norton, J. Am. Chem. Soc. 1996, 118, 3479, and references therein; c) C. Lefeber, P. Arndt, A. Tillack, W. Baumann, R. Kempe, V. V. Burlakov, U. Rosenthal, Organometallics 1995, 14, 3090; d) M. C. J. Harris, R. J. Whitby, Tetrahedron Lett. 1995, 36, 4287, and references therein; c) R. B. Grossman, W. M. Davis, S. L. Buchwald, J. Am. Chem. Soc. 1991, 113, 2321; f) M. Jensen, T. Livinghouse, J. Am. Chem. Soc. 1989, 111, 4495.
20. Zirconocene imine complexes: a) J. Barluenga, R. Sanz, F. J. Fananás, J. Org. Chem. 1997, 62, 5953; b) D. A. Gately, J. R. Norton, J. Am. Chem. Soc. 1996, 118, 3479, and references therein; c) C. Lefeber, P. Arndt, A. Tillack, W. Baumann, R. Kempe, V. V. Burlakov, U. Rosenthal, Organometallics 1995, 14, 3090; d) M. C. J. Harris, R. J. Whitby, Tetrahedron Lett. 1995, 36, 4287, and references therein; c) R. B. Grossman, W. M. Davis, S. L. Buchwald, J. Am. Chem. Soc. 1991, 113, 2321; f) M. Jensen, T. Livinghouse, J. Am. Chem. Soc. 1989, 111, 4495.
21. S. S. C. Koch, R. Chamberlin, J. Org. Chem. 1993, 58, 2725, and references therein.
22. J. M. Davis, R. J. Whitby, A. Jaxa-Chamiec, J. Chem. Soc., Chem. Commun. 1991, 1743.
23. J. Scholz, M. Nolte, C. Krüger, Chem. Ber. 1993, 126, 803.
24. Reviews on homoenolates: a) I. Kuwajima, E. Nakamura, Comprehensive Organic Synthesis 1991, 2, 441; b) N. H. Werstiuk in Umpoled Synthons (Ed.: T. A. Hase), Wiley, New York, 1987, pp. 173-216. Homoenolates in asymmetric syntheses: a) D. Hoppe, T. Hense, Angew. Chem. 1997, 109, 2376; Angew. Chem. Int. Ed. Engl. 1997, 36, 2282. and references therein; b) J. B. Schwarz, P. N. Devine, A. I. Meyers, Tetrahedron 1997, 53, 8795; c) M. Garcia-Valverde, R. Pedrosa, M. Vicente, S. García-Granda, A. Gutiérrez-Rodríguez, ibid. 1996, 52, 10761; d) J. D. Armstrong, F. W. Hardner, A. E. DeCamp, R. P. Volante, I. Shinkai, Tetrahedron Lett. 1992, 6599; e) H. Ahlbrecht, G. Bonnet, D. Enders, G. Zimmermann, Tetrahedron Lett. 1980, 21, 3175. Homoenolates in the syntheses of β,γ,γ-trisubstituted five-membered-ring oxygen heterocycles: e) A. R. Katritzky, D. Feng, H. Lang, J. Org. Chem. 1997, 62, 706; f) E. Alonso, D. J. Ramón, M. Yus, Tetrahedron 1997, 53, 2641.
25. Reviews on homoenolates: a) I. Kuwajima, E. Nakamura, Comprehensive Organic Synthesis 1991, 2, 441; b) N. H. Werstiuk in Umpoled Synthons (Ed.: T. A. Hase), Wiley, New York, 1987, pp. 173-216. Homoenolates in asymmetric syntheses: a) D. Hoppe, T. Hense, Angew. Chem. 1997, 109, 2376; Angew. Chem. Int. Ed. Engl. 1997, 36, 2282. and references therein; b) J. B. Schwarz, P. N. Devine, A. I. Meyers, Tetrahedron 1997, 53, 8795; c) M. Garcia-Valverde, R. Pedrosa, M. Vicente, S. García-Granda, A. Gutiérrez-Rodríguez, ibid. 1996, 52, 10761; d) J. D. Armstrong, F. W. Hardner, A. E. DeCamp, R. P. Volante, I. Shinkai, Tetrahedron Lett. 1992, 6599; e) H. Ahlbrecht, G. Bonnet, D. Enders, G. Zimmermann, Tetrahedron Lett. 1980, 21, 3175. Homoenolates in the syntheses of β,γ,γ-trisubstituted five-membered-ring oxygen heterocycles: e) A. R. Katritzky, D. Feng, H. Lang, J. Org. Chem. 1997, 62, 706; f) E. Alonso, D. J. Ramón, M. Yus, Tetrahedron 1997, 53, 2641.
26. Reviews on homoenolates: a) I. Kuwajima, E. Nakamura, Comprehensive Organic Synthesis 1991, 2, 441; b) N. H. Werstiuk in Umpoled Synthons (Ed.: T. A. Hase), Wiley, New York, 1987, pp. 173-216. Homoenolates in asymmetric syntheses: a) D. Hoppe, T. Hense, Angew. Chem. 1997, 109, 2376; Angew. Chem. Int. Ed. Engl. 1997, 36, 2282. and references therein; b) J. B. Schwarz, P. N. Devine, A. I. Meyers, Tetrahedron 1997, 53, 8795; c) M. Garcia-Valverde, R. Pedrosa, M. Vicente, S. García-Granda, A. Gutiérrez-Rodríguez, ibid. 1996, 52, 10761; d) J. D. Armstrong, F. W. Hardner, A. E. DeCamp, R. P. Volante, I. Shinkai, Tetrahedron Lett. 1992, 6599; e) H. Ahlbrecht, G. Bonnet, D. Enders, G. Zimmermann, Tetrahedron Lett. 1980, 21, 3175. Homoenolates in the syntheses of β,γ,γ-trisubstituted five-membered-ring oxygen heterocycles: e) A. R. Katritzky, D. Feng, H. Lang, J. Org. Chem. 1997, 62, 706; f) E. Alonso, D. J. Ramón, M. Yus, Tetrahedron 1997, 53, 2641.
27. Reviews on homoenolates: a) I. Kuwajima, E. Nakamura, Comprehensive Organic Synthesis 1991, 2, 441; b) N. H. Werstiuk in Umpoled Synthons (Ed.: T. A. Hase), Wiley, New York, 1987, pp. 173-216. Homoenolates in asymmetric syntheses: a) D. Hoppe, T. Hense, Angew. Chem. 1997, 109, 2376; Angew. Chem. Int. Ed. Engl. 1997, 36, 2282. and references therein; b) J. B. Schwarz, P. N. Devine, A. I. Meyers, Tetrahedron 1997, 53, 8795; c) M. Garcia-Valverde, R. Pedrosa, M. Vicente, S. García-Granda, A. Gutiérrez-Rodríguez, ibid. 1996, 52, 10761; d) J. D. Armstrong, F. W. Hardner, A. E. DeCamp, R. P. Volante, I. Shinkai, Tetrahedron Lett. 1992, 6599; e) H. Ahlbrecht, G. Bonnet, D. Enders, G. Zimmermann, Tetrahedron Lett. 1980, 21, 3175. Homoenolates in the syntheses of β,γ,γ-trisubstituted five-membered-ring oxygen heterocycles: e) A. R. Katritzky, D. Feng, H. Lang, J. Org. Chem. 1997, 62, 706; f) E. Alonso, D. J. Ramón, M. Yus, Tetrahedron 1997, 53, 2641.
28. Reviews on homoenolates: a) I. Kuwajima, E. Nakamura, Comprehensive Organic Synthesis 1991, 2, 441; b) N. H. Werstiuk in Umpoled Synthons (Ed.: T. A. Hase), Wiley, New York, 1987, pp. 173-216. Homoenolates in asymmetric syntheses: a) D. Hoppe, T. Hense, Angew. Chem. 1997, 109, 2376; Angew. Chem. Int. Ed. Engl. 1997, 36, 2282. and references therein; b) J. B. Schwarz, P. N. Devine, A. I. Meyers, Tetrahedron 1997, 53, 8795; c) M. Garcia-Valverde, R. Pedrosa, M. Vicente, S. García-Granda, A. Gutiérrez-Rodríguez, ibid. 1996, 52, 10761; d) J. D. Armstrong, F. W. Hardner, A. E. DeCamp, R. P. Volante, I. Shinkai, Tetrahedron Lett. 1992, 6599; e) H. Ahlbrecht, G. Bonnet, D. Enders, G. Zimmermann, Tetrahedron Lett. 1980, 21, 3175. Homoenolates in the syntheses of β,γ,γ-trisubstituted five-membered-ring oxygen heterocycles: e) A. R. Katritzky, D. Feng, H. Lang, J. Org. Chem. 1997, 62, 706; f) E. Alonso, D. J. Ramón, M. Yus, Tetrahedron 1997, 53, 2641.
29. Reviews on homoenolates: a) I. Kuwajima, E. Nakamura, Comprehensive Organic Synthesis 1991, 2, 441; b) N. H. Werstiuk in Umpoled Synthons (Ed.: T. A. Hase), Wiley, New York, 1987, pp. 173-216. Homoenolates in asymmetric syntheses: a) D. Hoppe, T. Hense, Angew. Chem. 1997, 109, 2376; Angew. Chem. Int. Ed. Engl. 1997, 36, 2282. and references therein; b) J. B. Schwarz, P. N. Devine, A. I. Meyers, Tetrahedron 1997, 53, 8795; c) M. Garcia-Valverde, R. Pedrosa, M. Vicente, S. García-Granda, A. Gutiérrez-Rodríguez, ibid. 1996, 52, 10761; d) J. D. Armstrong, F. W. Hardner, A. E. DeCamp, R. P. Volante, I. Shinkai, Tetrahedron Lett. 1992, 6599; e) H. Ahlbrecht, G. Bonnet, D. Enders, G. Zimmermann, Tetrahedron Lett. 1980, 21, 3175. Homoenolates in the syntheses of β,γ,γ-trisubstituted five-membered-ring oxygen heterocycles: e) A. R. Katritzky, D. Feng, H. Lang, J. Org. Chem. 1997, 62, 706; f) E. Alonso, D. J. Ramón, M. Yus, Tetrahedron 1997, 53, 2641.
30. Reviews on homoenolates: a) I. Kuwajima, E. Nakamura, Comprehensive Organic Synthesis 1991, 2, 441; b) N. H. Werstiuk in Umpoled Synthons (Ed.: T. A. Hase), Wiley, New York, 1987, pp. 173-216. Homoenolates in asymmetric syntheses: a) D. Hoppe, T. Hense, Angew. Chem. 1997, 109, 2376; Angew. Chem. Int. Ed. Engl. 1997, 36, 2282. and references therein; b) J. B. Schwarz, P. N. Devine, A. I. Meyers, Tetrahedron 1997, 53, 8795; c) M. Garcia-Valverde, R. Pedrosa, M. Vicente, S. García-Granda, A. Gutiérrez-Rodríguez, ibid. 1996, 52, 10761; d) J. D. Armstrong, F. W. Hardner, A. E. DeCamp, R. P. Volante, I. Shinkai, Tetrahedron Lett. 1992, 6599; e) H. Ahlbrecht, G. Bonnet, D. Enders, G. Zimmermann, Tetrahedron Lett. 1980, 21, 3175. Homoenolates in the syntheses of β,γ,γ-trisubstituted five-membered-ring oxygen heterocycles: e) A. R. Katritzky, D. Feng, H. Lang, J. Org. Chem. 1997, 62, 706; f) E. Alonso, D. J. Ramón, M. Yus, Tetrahedron 1997, 53, 2641.
31. Reviews on homoenolates: a) I. Kuwajima, E. Nakamura, Comprehensive Organic Synthesis 1991, 2, 441; b) N. H. Werstiuk in Umpoled Synthons (Ed.: T. A. Hase), Wiley, New York, 1987, pp. 173-216. Homoenolates in asymmetric syntheses: a) D. Hoppe, T. Hense, Angew. Chem. 1997, 109, 2376; Angew. Chem. Int. Ed. Engl. 1997, 36, 2282. and references therein; b) J. B. Schwarz, P. N. Devine, A. I. Meyers, Tetrahedron 1997, 53, 8795; c) M. Garcia-Valverde, R. Pedrosa, M. Vicente, S. García-Granda, A. Gutiérrez-Rodríguez, ibid. 1996, 52, 10761; d) J. D. Armstrong, F. W. Hardner, A. E. DeCamp, R. P. Volante, I. Shinkai, Tetrahedron Lett. 1992, 6599; e) H. Ahlbrecht, G. Bonnet, D. Enders, G. Zimmermann, Tetrahedron Lett. 1980, 21, 3175. Homoenolates in the syntheses of β,γ,γ-trisubstituted five-membered-ring oxygen heterocycles: e) A. R. Katritzky, D. Feng, H. Lang, J. Org. Chem. 1997, 62, 706; f) E. Alonso, D. J. Ramón, M. Yus, Tetrahedron 1997, 53, 2641.
32. Reviews on homoenolates: a) I. Kuwajima, E. Nakamura, Comprehensive Organic Synthesis 1991, 2, 441; b) N. H. Werstiuk in Umpoled Synthons (Ed.: T. A. Hase), Wiley, New York, 1987, pp. 173-216. Homoenolates in asymmetric syntheses: a) D. Hoppe, T. Hense, Angew. Chem. 1997, 109, 2376; Angew. Chem. Int. Ed. Engl. 1997, 36, 2282. and references therein; b) J. B. Schwarz, P. N. Devine, A. I. Meyers, Tetrahedron 1997, 53, 8795; c) M. Garcia-Valverde, R. Pedrosa, M. Vicente, S. García-Granda, A. Gutiérrez-Rodríguez, ibid. 1996, 52, 10761; d) J. D. Armstrong, F. W. Hardner, A. E. DeCamp, R. P. Volante, I. Shinkai, Tetrahedron Lett. 1992, 6599; e) H. Ahlbrecht, G. Bonnet, D. Enders, G. Zimmermann, Tetrahedron Lett. 1980, 21, 3175. Homoenolates in the syntheses of β,γ,γ-trisubstituted five-membered-ring oxygen heterocycles: e) A. R. Katritzky, D. Feng, H. Lang, J. Org. Chem. 1997, 62, 706; f) E. Alonso, D. J. Ramón, M. Yus, Tetrahedron 1997, 53, 2641.
33. Reviews on homoenolates: a) I. Kuwajima, E. Nakamura, Comprehensive Organic Synthesis 1991, 2, 441; b) N. H. Werstiuk in Umpoled Synthons (Ed.: T. A. Hase), Wiley, New York, 1987, pp. 173-216. Homoenolates in asymmetric syntheses: a) D. Hoppe, T. Hense, Angew. Chem. 1997, 109, 2376; Angew. Chem. Int. Ed. Engl. 1997, 36, 2282. and references therein; b) J. B. Schwarz, P. N. Devine, A. I. Meyers, Tetrahedron 1997, 53, 8795; c) M. Garcia-Valverde, R. Pedrosa, M. Vicente, S. García-Granda, A. Gutiérrez-Rodríguez, ibid. 1996, 52, 10761; d) J. D. Armstrong, F. W. Hardner, A. E. DeCamp, R. P. Volante, I. Shinkai, Tetrahedron Lett. 1992, 6599; e) H. Ahlbrecht, G. Bonnet, D. Enders, G. Zimmermann, Tetrahedron Lett. 1980, 21, 3175. Homoenolates in the syntheses of β,γ,γ-trisubstituted five-membered-ring oxygen heterocycles: e) A. R. Katritzky, D. Feng, H. Lang, J. Org. Chem. 1997, 62, 706; f) E. Alonso, D. J. Ramón, M. Yus, Tetrahedron 1997, 53, 2641.
34. E.-I. Negishi, S. J. Holmes, J. M. Tour, J. A. Miller, F. E. Cederbaum, D. R. Swanson, T. Takahashi, J. Am. Chem. Soc. 1989, 111, 3336.
35. V. K. Dioumaev, J. F. Harrod. Organometallics 1997, 16, 1452; see also D. R. Swanson, E.-I. Negishi, Organometallics 1991, 10, 825.
36. V. K. Dioumaev, J. F. Harrod. Organometallics 1997, 16, 1452; see also D. R. Swanson, E.-I. Negishi, Organometallics 1991, 10, 825.
37. [2] A gas outlet for the removal of these by-products should, therefore, have a positive effect on the driving force of the complexation as well as on the prevention of side reactions. This is proved by obtaining near quantitative yields when a stream of argon is passed over the reaction mixture.
38. C. Glacet, Bull. Soc. Chim. Fr. 1952, 990, 994.
39. a) Y. Koga, M. Sodeoka, M. Shibasaki. Tetrahedron Lett. 1994, 35, 1227;
40. b) T. Sakamoto, Y. Kondo, H. Yamanaka, Heterocycles 1993, 36, 2437.
41. -3. Crystallographic data (excluding structure factors) for the structure reported in this paper have been deposited with the Cambridge Crystallographic Data Centre as supplementary publication no. CCDC-101110. Copies of the data can be obtained free of charge on application to CCDC, 12 Union Road, Cambridge CB21EZ, UK (fax: (+44)1223-336-033; e-mail: deposit@ccdc.cam. ac.uk).
42. S. R. Hall, H. D. Flack, J. M. Stewart, XTAL3.2 Reference Manual, Universities of West-Australia, Genf and Maryland, Lamb, Perth, 1992.
43. Software for ball and-stick plot: Ball & Stick Ver. 2.2. A. Falk, N. Müller, G. Schoppel, L. Webb, Linz (Austria), Stafford (UK).
44. All isolated new compounds showed suitable spectroscopic data (IR, NMR, MS) and correct elemental analysis or high resolution mass spectra.